4-Hydroxymethylpyridine → HCID 20491775, compound
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.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=1.C(Cl)(Cl)Cl.C(O)C>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:31][C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)[CH:23]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (522 mg) and 4-pyridylcarbinol (611 mg) in dry N,N-dimethylformamide (10 ml) under nitrogen and the the mixture was then heated at 90° C. After 41/2 h the reaction mixture was evaporated to a brown solid which was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 14:1. This gave a yellow crystalline solid which was subjected to p.l.c. on silica developing with chloroform-ethanol, 9:1 (three runs). The major band was eluted with chloroform-ethanol, 1:1, to give a pale yellow foam which was crystallised from acetone to give off white crystals of the title pyrimidinone (210 mg), m.p. 205°-206° C., λmax (EtOH) 246 nm (ε 7.050), 332.5 nm (ε 950).
Workup
- customAfter 41/2 h the reaction mixture was evaporated to a brown solid which
- washeluting with chloroform-ethanol, 14:1
- customThis gave a yellow crystalline solid which
- washThe major band was eluted with chloroform-ethanol, 1:1
- customto give a pale yellow foam which
- customwas crystallised from acetone
Sources & evidence
- ORD record
- ord-8d6d39ca55b241058e46fbacdb4f6ae7
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04399140
Reaction notes
Loading…