1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → 5-Chloro-1-(1-methylpyrrol-2-ylmethyl)pyrimidin-2-one
Reaction equation
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.[CH3:25][N:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[CH2:31]O>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:31][C:27]2[N:26]([CH3:25])[CH:30]=[CH:29][CH:28]=2)[CH:23]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
N,N-Dimethylformamide dineopentyl acetal (3.04 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (881 mg) and N-methyl-2-hydroxymethylpyrrole (1.050 g) in dry N,N-dimethylformamide (17 ml) under nitrogen. The resulting pale yellow solution was then stirred and heated at 90° C. under nitrogen. After 1 h the reaction mixture was evaporated to a brown crystalline solid (1.891 g). The solid was subjected to column chromatography on silica (70-230 mesh) (200 g) developing with chloroform-ethanol, 29:1. The resulting pale brown crystalline solid (1.479 g) was crystallised twice from acetone to give off white needles of the title pyrrole (559 mg), m.p. 137°-141° C., λmax 226.5 nm (ε 15,920), 334 nm (ε 2,680).
Workup
- customAfter 1 h the reaction mixture was evaporated to a brown crystalline solid (1.891 g)
- customThe resulting pale brown crystalline solid (1.479 g) was crystallised twice from acetone
Sources & evidence
- ORD record
- ord-dc2de2038ef44837a239db5ff6318962
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04399140
Reaction notes
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