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

HRID 247086Notes

Reaction equation

HRID 247086 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, J3Hz).

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-3e8c6626a906487a81d3de1d4b4030f1
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

Loading…