Triethylamine → 1-(4-Hydroxymethylphenylthiomethyl)-5-chloropyrimidin-2-one

HRID 1982573Notes

Reaction equation

HRID 1982573 reaction equation
Cl[CH2:2][S:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.Cl.[Cl:13][C:14]1[CH:15]=[N:16][C:17](=[O:20])[NH:18][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[OH:9][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([S:3][CH2:2][N:18]2[CH:19]=[C:14]([Cl:13])[CH:15]=[N:16][C:17]2=[O:20])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 538676354-(Chloromethylthio) benzyl alcohol

Product 1

HCID 201613391-(4-Hydroxymethylphenylthiomethyl)-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(Chloromethylthio) benzyl alcohol (see Preparation 17) (5 mmol) in CH2Cl2 (2 ml) was added dropwise with stirring to a solution prepared from 5-chloropyrimidin-2-one hydrochloride (4 mmol) and triethylamine (8 mmol) in CH2Cl2 (20 ml). The resultant mixture was heated under reflux for 24 hours. The solvent was then distilled off, the residue triturated with water, dried (MgSO4), triturated with ether and the residual material recrystallized from ethanol/Pet. ether. Yield 0.17 g (15%). 1H NMR (DMSO-d6, δ) 4.50 (CH2O), 5.22 (CH2S), 7.22 (Ph), 8.03 or 8.50 (H-4, H-6, J3 Hz).

Workup

  1. temperatureunder reflux for 24 hours
  2. distillationThe solvent was then distilled off
  3. customthe residue triturated with water
  4. dry with materialdried (MgSO4)
  5. customtriturated with ether
  6. customthe residual material recrystallized from ethanol/Pet. ether

Sources & evidence

ORD record
ord-4e30044ef1da45e9b976da9ae0c5e0f9
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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