ChemicalBook > CAS DataBase List > 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE

5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE

Uses

Product Name: 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE
CAS No.: 38696-21-8
Chemical Name: 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE
Synonyms: 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE;(5-BROMOPYRIMIDIN-2-YL)DIMETHYLAMINE;5-Bromo-N,N-dimethylpyrimidin-2-amine;5-Bromo-N,N-dimethyl-2-pyrimidinamine;2-broMo-N,N-diMethylpyriMidin-4-aMine;2-Pyrimidinamine, 5-bromo-N,N-dimethyl-;5-Bromo-2-(dimethylamino)pyrimidine 97%;5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE ISO 9001：2015 REACH
CBNumber: CB5472682
Molecular Formula: C6H8BrN3
Formula Weight: 202.05
MOL File: 38696-21-8.mol

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5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE Property

Melting point:: 74-81°C
Boiling point:: 272.0±32.0 °C(Predicted)
Density: 1.553±0.06 g/cm3(Predicted)
storage temp.: 2-8°C(protect from light)
form: solid
pka: 2.21±0.10(Predicted)
color: off white
InChI: InChI=1S/C6H8BrN3/c1-10(2)6-8-3-5(7)4-9-6/h3-4H,1-2H3
InChIKey: NYMYGNLCILQUMT-UHFFFAOYSA-N
SMILES: C1(N(C)C)=NC=C(Br)C=N1

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Safety

Hazard Codes: Xi,Xn
Risk Statements: 22-36/37/38
Safety Statements: 26-36/37
WGK Germany: 3
Hazard Note: Irritant
HS Code: 2933599590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 701955
Product name: 5-Bromo-2-(dimethylamino)pyrimidine
Purity: 97%
Packaging: 1g
Price: $130
Updated: 2023/06/20

Sigma-Aldrich

Product number: 701955
Product name: 5-Bromo-2-(dimethylamino)pyrimidine
Purity: 97%
Packaging: 5g
Price: $302
Updated: 2022/05/15

TRC

Product number: B677833
Product name: 5-Bromo-2-(dimethylamino)pyrimidine
Packaging: 100mg
Price: $75
Updated: 2021/12/16

SynQuest Laboratories

Product number: 3H32-9-1D
Product name: 5-Bromo-2-(dimethylamino)pyrimidine
Packaging: 1g
Price: $16
Updated: 2021/12/16

AK Scientific

Product number: X7054
Product name: 5-Bromo-2-(dimethylamino)pyrimidine
Packaging: 1g
Price: $68
Updated: 2021/12/16

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5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE Chemical Properties,Usage,Production

Uses

5-Bromo-2-(dimethylamino)pyrimidine is a common pharmaceutical and chemical intermediate. Pyrimidines are important bioactive molecular structures, and their role as fundamental building blocks in new drug design and synthesis has long attracted attention. Studies have shown that different substitution modifications on the pyrimidine ring significantly affect its physiological activity. For example, 2,4-diaminopyrimidine derivatives exhibit good inhibitory activity against protein tyrosine phosphatase 1B; 2-amino-4-alkoxypyrimidine derivatives exhibit bioactivity against cyclin-dependent kinases; pyrimidine thiourea compounds exhibit neuraminidase inhibitory activity, and so on. All the bioactive compounds reported in the literature above contain a 2-substituted aminopyrimidine structure.

Chemical Properties

Off-White crystal

Synthesis

7752-82-1

74-88-4

38696-21-8

General procedure for the synthesis of 5-bromo-2-(dimethylamino)pyrimidines from 2-amino-5-bromopyrimidines and iodomethane: 1. preparation of the related pyran(mi)dihalides A-H. Key steps include: (a) 85-90% yield of pyridine; quantitative yield of pyrimidine using NBS and NH4OAc in MeCN at room temperature for 5 min; (b) Pyridine: refluxed with RCHO and Na(CN)BH3 in MeCN for 1-12 hr (82%, R=C5Hn); pyrimidine: using NaH and R1 in THF, overnight at room temperature (85%, R=Me); (c) Pyridine yield 77-83%; pyrimidine yield 30-40% using Me3(Bn)NBr and f-BuONO in CH2Br2, overnight at room temperature; (d) Pyrimidine: reaction using HI in CH2Cl2 at 0°C, 80-85% yield; (e) Steps included: i. reaction using NaOH and Br2 in aqueous solution, room temperature, 50-60% yield; ii. refluxing using POCl3 and PhNEt2 for 4 hrs, 75-85% yield; iii. reaction using HI in CH2Cl2, 0 °C, 80-85% yield; (f) Reaction using ROH and Na at room temperature for 1-12 hr in quantitative yield; (g) Use of RZnI and Cl2Pd(PPh3)2 in DMF/THF overnight at room temperature in 72% (R=C6H13) yield for pyridine (Br) and 81% (R=C6H13) yield for pyrimidine (I); (h) Quantitative yields using alkynes, Cul, Cl2Pd(PPh3)2, and Et3N in MeCN, reacted for 1-12 h at room temperature. Pyrimidinyl bromides were prepared in a similar manner starting from the bromination of 2-aminopyrimidine. N-alkylation could not be achieved by reductive amination (probably due to the reduced nucleophilicity of the amine), but N-(B) was achieved using NaH and the appropriate alkyl halide. Non-aqueous diazotization/halogenated deoxidation was used to prepare 5-bromo-2-halogenated pyrimidines, but in reduced yield relative to a similar reaction with 2-aminopyridine (again, possibly due to reduced nucleophilicity of the amine group). Alternatively, 2-pyrimidinone can be used as a precursor to 5-bromo-2-halopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006,17,486) or as a substrate for alkylation. Generation of 5-bromo-2-alkoxypyrimidines (D) (Kokatla, HP; Lakshman, MK Org. Lett. 2010,12,4478.) was obtained by introduction of an alkynyl substituent at the 2-position (which was carried out satisfactorily under Sonogoshira conditions, but alkylation using Negishi conditions was non-selective. Since 2-alkynylpyrimidinyl bromides (F) were competitively removed due to the reduction of 2-alkynylpyrimidinyl bromides (H) to the corresponding 2-alkylpyrimidinyl bromides (H), we turned to 5-bromo-2-iodopyrimidines as precursors for the cross-coupling reaction, with a significant increase in selectivity and yield.

References

[1] Patent: WO2012/162818, 2012, A1. Location in patent: Page/Page column 45-46
[2] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333

5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE Preparation Products And Raw materials

Raw materials

Nitrogen Ethanol 5-Bromo-2-chloropyrimidine 2-Aminopyrimidine Lithium amide Diethyl ether Benzene Ethyl acetate Sodium bicarbonate Dichloromethane 1,3-Dibromo-5,5-dimethylhydantoin Dimethylamine PETROLEUM ETHER Iodomethane

Preparation Products

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View Lastest Price from 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE manufacturers

Dideu Industries Group Limited

Product: 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE 38696-21-8
Price: US $1.10/g
Min. Order: 1g
Purity: 99.00%
Supply Ability: 100 Tons Min
Release date: 2021-12-01

Career Henan Chemical Co

Product: 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE 38696-21-8
Price: US $1.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 200KG
Release date: 2018-12-19

38696-21-8, 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINERelated Search:

5-BROMO-2-MORPHOLIN-1-YL-PYRIMIDINE 5-BROMO-2-(PYRROLIDIN-1-YL)PYRIMIDINE N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE 1-(5-BROMOPYRIMIDIN-2-YL)PIPERIDINE-4-CARBOXYLIC ACID 1-(5-Bromopyrimidin-2-yl)piperidine-3-carboxylic acid 1-(5-BROMOPYRIMIDIN-2-YL)[1,4]DIAZEPANE 1-(5-BROMOPYRIMIDIN-2-YL)-4-PIPERIDINOL 4-(5-BROMO-PYRIMIDIN-2-YL)-2,6-DIMETHYL-MORPHOLINE 5-BROMO-2-(4-METHYLPIPERAZIN-1-YL)PYRIMIDINE 2-[4-(5-BROMOPYRIMIDIN-2-YL)PIPERAZIN-1-YL]ETHANOL 5-Bromo-2-(piperidin-1-yl)pyrimidine (5-BROMO-PYRIMIDIN-2-YL)-DIETHYL-AMINE 5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE-4-CARBOXYLIC ACID 5-BROMO-2-(4-PYRIDIN-2-YLPIPERAZIN-1-YL)PYRIMIDINE DIBENZYL-(5-BROMO-PYRIMIDIN-2-YL)-AMINE 2-(4-BENZHYDRYLPIPERAZIN-1-YL)-5-BROMOPYRIMIDINE N-ALLYL-N-(5-BROMO-4-METHOXY-6-METHYLPYRIMIDIN-2-YL)ACETAMIDE BENZYL-(5-BROMO-PYRIMIDIN-2-YL)-METHYL-AMINE

5-Bromo-N,N-dimethyl-2-pyrimidinamine

5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE

(5-BROMOPYRIMIDIN-2-YL)DIMETHYLAMINE

5-Bromo-N,N-dimethylpyrimidin-2-amine

2-Pyrimidinamine, 5-bromo-N,N-dimethyl-

2-broMo-N,N-diMethylpyriMidin-4-aMine

5-Bromo-2-(dimethylamino)pyrimidine 97%

5-BROMO-2-(DIMETHYLAMINO)PYRIMIDINE ISO 9001：2015 REACH

38696-21-8

Heterocycle-Pyrimidine series

Pyrimidine

Amino

Organohalides