3-Pyridinemethanol → HCID 20491770, compound

HRID 434650Notes

Reaction equation

HRID 434650 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][CH:28]=[C:27]([CH2:31]O)[CH:26]=1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 20491770HCID 20491770, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 3-pyridylcarbinol (0.55 ml) in dry N,N-dimethylformamide (10 ml) under nitrogen and the mixture was then heated at 90° C. After 1 h the reaction mixture was evaporated to a brown solid which was subjected to column chromatography on silica developing one eluting with chloroform-ethanol, 14:1. This gave a pale yellow solid which was crystallised from acetone to give off white needles of the title pyrimidinone (387 mg), m.p. 191°-193° C., λmax (EtOH) 229.5 nm (ε 8,930), 334 nm (ε 2,530).

Workup

  1. customAfter 1 h the reaction mixture was evaporated to a brown solid which
  2. customThis gave a pale yellow solid which
  3. customwas crystallised from acetone

Sources & evidence

ORD record
ord-42e71fd0eeb346bc95cd6774be99a91f
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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