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

HRID 434654Notes

Reaction equation

HRID 434654 reaction equation
C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[I: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>[I: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 119590965-Iodopyrimidin-2-ol

Product 1

HCID 204917515-Iodo-1-(2-thienylmethyl)pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide dineopentyl acetal (1.5 ml) was added to a stirred suspension of 5-iodopyrimidin-2-one (777 mg) and 2-hydroxymethyl thiophene (0.62 ml) in dry N,N-dimethylformamide (8 ml) under nitrogen and the mixture was then heated at 80° C. After 13/4 h the reaction mixture was evaporated to a brown solid which was crystallised twice from ethyl acetate to give the title pyrimidinone (540 mg), m.p. 207°-209° C., λmax (EtOH) 232.5 nm (ε 21,820), 341.5 nm (ε 2,420).

Workup

  1. customAfter 13/4 h the reaction mixture was evaporated to a brown solid which
  2. customwas crystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-4b68c419706f48f0aab3fffae9657d4e
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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