Hydrochloric Acid → Methyl 2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formate
Reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([CH3:11])[N:5]=1.Cl[C:13]1[S:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:17]=1.Cl>C1COCC1>[Br:10][C:8]1[N:7]=[C:6]([CH3:11])[N:5]=[C:4]([NH:3][C:13]2[S:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:17]=2)[CH:9]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
60% sodium hydride (12.0 g, 0.30 mol) was suspended in THF (300 mL) and cooled down to 0° C. 4-amino-6-bromo-2-methylpyrimidine (Compound 9) (18.7 g, 0.1 mol) was then added in batches and stirred for 30 min. After methyl 2-chlorothiazole-5-formate (Compound 10) (17.7 g, 0.1 mol) was added in batches, the reactants were heated and reacted by refluxing for 4 h, and then cooled down to room temperature for reaction overnight. When controlling the temperature between 0° C. and 5° C., hydrochloric acid (2N) was added for neutralization reaction. After adding keep heat and stirred to grow grains for 1 h. Filtrate and wash the cake with water, and then dry to give target Compound 11 (25.8 g, yield is 78.4%).
Workup
- temperaturethe reactants were heated
- customreacted
- temperatureby refluxing for 4 h
- temperaturecooled down to room temperature for reaction overnight
- additionwas added for neutralization reaction
- additionAfter adding keep
- temperatureheat
- stirringstirred
- customfor 1 h
- washFiltrate and wash the cake with water
- customdry
Sources & evidence
- ORD record
- ord-5b795298847a425e8aeb14da61765404
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108954B2
Reaction notes
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