Triethylamine → 1-(3-Methylphenylthio)methyl-5-fluoropyrimidin-2-one

HRID 1982567Notes

Reaction equation

HRID 1982567 reaction equation
Cl[CH2:2][S:3][C:4]1[CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1.[F:11][C:12]1[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=1.C(N(CC)CC)C.[K+].[Br-]>ClCCl>[CH3:10][C:6]1[CH:5]=[C:4]([S:3][CH2:2][N:16]2[CH:17]=[C:12]([F:11])[CH:13]=[N:14][C:15]2=[O:18])[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1014985-Fluoropyrimidin-2-oneHCID 253877Potassium BromideHCID 128408943-Methylphenyl chloromethyl sulfide

Product 1

HCID 156505001-(3-Methylphenylthio)methyl-5-fluoropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Chloromethylthio)toluene (6.5 mmol) was added to a solution of 5-fluoropyrimidin-2-one (6.5 mmol) and triethylamine (6.5 mmol) in dichloromethane (75 ml) and the resultant mixture heated under reflux for 2 days. The solvent was then distilled off, the residue triturated with water and the residual material extracted with CCl4. Evaporation of the extracts and crystallisation of the residue from ethyl acetate gave the pure product; 0.40 g (25%), m.p. 124° C. (Found: C57.42; H4.63. Calc. for C12H11FN2OS: C57.59; H4.43) 1H NMR (DMSO d6); δ 2.28 (Me), 5.17(CH2), 7.2 (Ph), 8.05 (H-4), 8.70 (H-6). IR (KBr): 1670 cm-1 (CO), MS [70 eV, m/z (% rel. int.)]: 250 (8,M), 137(11), 136)36), 135(10), 128(7), 127(100), 100(34), 91(9).

Workup

  1. temperatureunder reflux for 2 days
  2. distillationThe solvent was then distilled off
  3. customthe residue triturated with water
  4. extractionthe residual material extracted with CCl4
  5. customEvaporation of the extracts and crystallisation of the residue from ethyl acetate
  6. customgave the pure product

Sources & evidence

ORD record
ord-229255d0db2347b2bea28eaa4d01f0b9
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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