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

HRID 434639Notes

Reaction equation

HRID 434639 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.O[CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 694672-ThiophenemethanolHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 1014945-Bromo-2(1H)-pyrimidinone

Product 1

HCID 204917745-Bromo-1-(2-thienylmethyl)pyrimidin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromopyrimidin-2-one (10 mmol), 2-hydroxymethylthiophene (36 mmol) and N,N-dimethylformamide dineopentyl acetal (15 mmol) in DMF (40 ml) were heated together at 80° C. for 150 min. The coloured solution was evaporated to dryness at reduced pressure (1 mmHg), the residual viscous material triturated with pet, ether (2×25 ml) and with ether (50 ml) when it solidified. This material was dissolved in chloroform and chromatographed on alumina (20 g, activity III). The title compound was eluted with chloroform; yield 48%, m.p. 188°-190° C. (EtOAc). 1H NMR (TFA) δ 5.68 (CH2); 7.18, 7.41, 7.58 (H3', H4', H5'), 8.95 (H4, H6).

Workup

  1. customThe coloured solution was evaporated to dryness at reduced pressure (1 mmHg)
  2. customthe residual viscous material triturated with pet, ether (2×25 ml) and with ether (50 ml) when it
  3. dissolutionThis material was dissolved in chloroform
  4. customchromatographed on alumina (20 g, activity III)
  5. washThe title compound was eluted with chloroform

Sources & evidence

ORD record
ord-84e55fbe29e94174807247deafb56f60
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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