2-Thiophenemethanol → 5-Fluoro-1-(2-thienylmethyl)pyrimidin-2-one

HRID 434653

Reaction equation

HRID 434653 reaction equation
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[F:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.O[CH2:26][C:27]1[S:28][CH:29]=[CH:30][CH:31]=1>CN(C)C=O>[F:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[N:22]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 694672-ThiophenemethanolHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1014985-Fluoropyrimidin-2-one

Product 1

HCID 204917665-Fluoro-1-(2-thienylmethyl)pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (1.76 ml) was added to a stirred suspension of 5-fluoropyrimidin-2-one (456 mg) and 2-hydroxymethyl thiophene (0.7 ml) in dry N,N-dimethylformamide (8 ml) under nitrogen and the mixture was then heated at 80° C. After 1 h the reaction mixture was evaporated to a brown solid which was crystallised twice from ethyl acetate to give white crystals of the title pyrimidinone (230 mg), m.p. 161°-163° C., λmax (EtOH) 222.5 nm (ε 10,890), 333.5 nm (ε 3,660).

Workup

  1. customAfter 1 h the reaction mixture was evaporated to a brown solid which
  2. customwas crystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-5bc85e7cc35d42269052212a80fa49d0
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Linked notes

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