4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-
- Product Name
- 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-
- CAS No.
- 706811-25-8
- Chemical Name
- 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy-
- Synonyms
- Macitentan Impurity 25;Macitentan Impurity 25 CRS;5-(4-broMophenyl)pyriMidine-4,6-diol;5-(4-Bromophenyl)-4,6-pyrimidinediol;5-(4-Bromophenyl)-4,6-dihydroxpyrimidine;5-(4-broMophenyl)pyriMidine-4,6(1H,5H)-dione;5-(4-bromophenyl)-6-hydroxypyrimidin-4(3H)-one;5-(4-bromophenyl)-4-hydroxy-1H-pyrimidin-6-one;5-(4-Bromophenyl)-6-hydroxypyrimidin-4(1H)-one;5-(4-broMophenyl)-6-hydroxy- 4(1H)-PyriMidinone
- CBNumber
- CB72623954
- Molecular Formula
- C10H7BrN2O2
- Formula Weight
- 267.08
- MOL File
- 706811-25-8.mol
4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy- Property
- Density
- 1.74±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 4.69±0.10(Predicted)
- Appearance
- White to yellow Solid
- InChI
- InChI=1S/C10H7BrN2O2/c11-7-3-1-6(2-4-7)8-9(14)12-5-13-10(8)15/h1-5H,(H2,12,13,14,15)
- InChIKey
- PIUMVXYVNAISNG-UHFFFAOYSA-N
- SMILES
- C1NC(O)=C(C2=CC=C(Br)C=C2)C(=O)N=1
Safety
- HS Code
- 2933599590
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 0056AP
- Product name
- 4(1H)-Pyrimidinone,5-(4-bromophenyl)-6-hydroxy
- Packaging
- 1g
- Price
- $80
- Updated
- 2021/12/16
- Product number
- OR55029
- Product name
- 5-(4-Bromophenyl)pyrimidine-4,6-diol
- Packaging
- 1g
- Price
- $182
- Updated
- 2021/12/16
- Product number
- 4H56-9-9D
- Product name
- 5-(4-Bromophenyl)pyrimidine-4,6-diol
- Packaging
- 1g
- Price
- $200
- Updated
- 2021/12/16
- Product number
- OR55029
- Product name
- 5-(4-Bromophenyl)pyrimidine-4,6-diol
- Packaging
- 5g
- Price
- $508
- Updated
- 2021/12/16
- Product number
- 4H56-9-9D
- Product name
- 5-(4-Bromophenyl)pyrimidine-4,6-diol
- Packaging
- 5G
- Price
- $560
- Updated
- 2021/12/16
4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy- Chemical Properties,Usage,Production
Uses
5-(4-Bromophenyl)pyrimidine-4,6-diol is used in preparation of pharmaceutical intermediate of Macitentan.
Synthesis
77287-34-4
149506-35-4
706811-25-8
To a stirred solution of 100 g of dimethyl 2-(4-bromophenyl)malonate (0.348 mol) dissolved in 400 cm3 methanol at 20-25 °C, 30 g of formamide (0.66 mol) and 30 g of sodium methanolate (0.555 mol) were added sequentially. The reaction mixture was heated to 70 °C and maintained at this temperature until the reaction was complete (monitored by HPLC). After completion of the reaction, methanol was removed by distillation under reduced pressure at 70°C to give a syrupy substance. The syrup was cooled to 25-30 °C and diluted with 2 dm3 water. The pH of the solution was adjusted to 2-2.5 with concentrated hydrochloric acid and this pH was maintained for 45 min. The precipitated solid was collected by filtration and washed with water until the filtrate reached pH 7-7.5. The product was blotted dry and dried under reduced pressure at 100°C to give the crude product 5-(4-bromophenyl)-6-hydroxypyrimidin-4(1H)-one. The crude product was dissolved in 500 cm3 methanol and heated to 60-65°C and kept for 1 hour. The reaction mixture was then cooled to 25-30°C and left to stand for 30 minutes. The resulting solid was filtered, washed with methanol and dried under reduced pressure at 50-55°C to give the pure product 5-(4-bromophenyl)-6-hydroxypyrimidin-4(1H)-one. Yield: 70 g (75.25%); HPLC purity: 99.5%; melting point: 176-180 °C. The spectral data of the obtained compounds were in agreement with literature reports [8].
References
[1] Monatshefte fur Chemie, 2018, vol. 149, # 3, p. 653 - 661
4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy- Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy- manufacturers
- Product
- 5-(4-Bromophenyl)-6-hydroxy-4(1H)-pyrimidinone 706811-25-8
- Price
- US $2.00-5.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-07-24
- Product
- 4(1H)-PyriMidinone, 5-(4-broMophenyl)-6-hydroxy- 706811-25-8
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 90%-99.9%
- Supply Ability
- 500kg
- Release date
- 2019-07-05