5-Chloro-2(1H)-pyrimidinone → 5-Chloro-1-(3-furoylmethyl)pyrimidin-2-one

HRID 1906150Notes

Reaction equation

HRID 1906150 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 186125513-Bromoacetylfuran

Product 1

HCID 127912445-Chloro-1-(3-furoylmethyl)pyrimidin-2-oneYield 31.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (587 mg) and crude 3-bromoacetylfuran (2.00 g, ca. 4.5 mmol, based on purity ca. 40% by 1H n.m.r; contaminated with 3-dibromoacetylfuran and diethyl ether) in triethylamine (0.95 ml) and ethanol (25 ml) was stirred at room temperature. After 45 min with solvent was removed and the residue triturated with ethyl acetate. The resulting solid was collected and retriturated with water. This gave a buff solid which was crystallised from ethyl acetate to give the title pyrimidinone (335 mg), m.p. 195°-197° C. (dec), λmax (EtOH) 333 nm (ε 2,530).

Workup

  1. customAfter 45 min with solvent was removed
  2. customthe residue triturated with ethyl acetate
  3. customThe resulting solid was collected
  4. customretriturated with water
  5. customThis gave a buff solid which
  6. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-6e8a7b94c0684666a0c46504021d0e00
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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