ChemicalBook > CAS DataBase List > 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product Name
4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
CAS No.
7781-10-4
Chemical Name
4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
Synonyms
NSC 102340;4-Chloro-7-methyl-7H-pyrr...;6-Chloro-9-Methyl-7-deazapurine;4-Chloro-7-methylpyrrolo[2,3-d]pyrimidine;4-Chlor-7-methyl-7H-pyrrolo[2,3-d]pyrimidine;4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine;7H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-7-methyl-;4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine;JR-14006, 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 96%;5-chloro-9-methyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-te...
CBNumber
CB91116648
Molecular Formula
C7H6ClN3
Formula Weight
167.6
MOL File
7781-10-4.mol
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4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Property

Melting point:
130 °C
Boiling point:
301.5±22.0 °C(Predicted)
Density 
1.43±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Dichloromethane, Ethyl Acetate, Methanol
pka
3.16±0.30(Predicted)
form 
Solid
color 
Light Brown
InChI
InChI=1S/C7H6ClN3/c1-11-3-2-5-6(8)9-4-10-7(5)11/h2-4H,1H3
InChIKey
BJGDLOLPALCTJQ-UHFFFAOYSA-N
SMILES
C1=NC(Cl)=C2C=CN(C)C2=N1
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Safety

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN2811
HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
JRD0459
Product name
4-Chloro-7-methyl-7<I>H</I>-pyrrolo[2,3-<I>d</I>]pyrimidine
Purity
Aldrich<SUP>CPR</SUP>
Packaging
1 g
Price
$259
Updated
2025/07/31
TRC
Product number
C366995
Product name
6-Chloro-9-methyl-7-deazapurine
Packaging
250mg
Price
$170
Updated
2021/12/16
Usbiological
Product number
006332
Product name
6-Chloro-9-methyl-7-deazapurine
Packaging
250mg
Price
$475
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
63636
Product name
6-Chloro-9-methyl-7-deazapurine
Packaging
250mg
Price
$660
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC140698
Product name
4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
Packaging
10g
Price
$668.8
Updated
2021/12/16
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4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties,Usage,Production

Chemical Properties

Light Brown Solid

Uses

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is used in the preparation of indoline derivatives as PERK inhibitors.

Synthesis

3680-69-1

74-88-4

7781-10-4

The general procedure for the synthesis of 4-chloro-7-methylpyrrolo[2,3-D]pyrimidine from 4-chloropyrrolopyrimidine and iodomethane was as follows: iodomethane (12.2 mL, 195 mmol) was added slowly and dropwise to a solution containing 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 97.7 mmol) and cesium carbonate (47.7 g, 146.5 mmol) in a N,N-dimethylformamide (DMF, 200 mL) solution. The reaction mixture was stirred at room temperature for 1 h. The reaction was subsequently quenched with deionized water (500 mL). The reaction mixture was extracted with ethyl acetate (3 x 200 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Purification of the crude product by fast column chromatography (silica gel, gradient elution with ethyl acetate:hexane, 2:8 to 3:7) afforded 4-chloro-7-methylpyrrolo[2,3-D]pyrimidine as an off-white solid (15.4 g, 94% yield). Mass Spectrometry (MS): m/z 168.5 ([M+H]+); High Performance Liquid Chromatography (HPLC) retention time (Rf): 3.45 min (HPLC method 4); HPLC purity: 96%.

References

[1] Patent: WO2004/56830, 2004, A1. Location in patent: Page 93
[2] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2153 - 2157
[3] Patent: WO2017/46739, 2017, A1. Location in patent: Page/Page column 89
[4] Patent: WO2018/194885, 2018, A1. Location in patent: Page/Page column 15
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7193 - 7207

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine Suppliers

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View Lastest Price from 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
6-Chloro-9-Methyl-7-deazapurine 7781-10-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20T
Release date
2020-05-15

7781-10-4, 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineRelated Search:

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine 7-BENZYL-4-CHLORO-5,6-DIPHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 7-ALLYL-4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE ETHYL 4-CHLORO-5-METHYL-7-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE-6-CARBOXYLATE 4-CHLORO-7-(3-CHLORO-4-METHYLPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 6-CHLORO-7-DEAZA-9-(2',3',5'-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL)PURINE 4-CHLORO-7-(4-FLUOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-7-(4-CHLOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-7-(4-METHYLPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 6-Chloro-7-deazapurine-b-D-riboside 4-CHLORO-5-PHENYL-7-[3-(TRIFLUOROMETHYL)PHENYL]-7H-PYRROLO[2,3-D]PYRIMIDINE 6-Chloro-7-deaza-9-(5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-b-D-ribofuranosyl)purine 4-CHLORO-7-(4-METHOXYPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 7-(4-BROMOPHENYL)-4-CHLORO-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-7-(2-FURYLMETHYL)-5,6-DIMETHYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-7-(3-CHLOROPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-7-(4-ETHOXYPHENYL)-5-PHENYL-7H-PYRROLO[2,3-D]PYRIMIDINE

  • 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
  • 4-Chloro-7-methyl-7H-pyrr...
  • 6-Chloro-9-Methyl-7-deazapurine
  • NSC 102340
  • 4-Chlor-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
  • 4-Chloro-7-methylpyrrolo[2,3-d]pyrimidine
  • JR-14006, 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 96%
  • 7H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-7-methyl-
  • 5-chloro-9-methyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-te...
  • 5-Chloro-9-methyl-2,4,9-triazabicyclo[4.3.0]nona-2,4,7,10-tetraene
  • 4-Chloro-7-methyl-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidine
  • 7781-10-4
  • 81-10-4
  • Bases & Related Reagents
  • Heterocycles
  • Intermediates
  • Nucleotides
  • Heterocycle-Pyrimidine series