HCID 11658340, compound → HCID 20161345, compound

HRID 247077Notes

Reaction equation

HRID 247077 reaction equation
Cl[CH2:2][S:3][C:4]1[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=1.Cl.[Cl:11][C:12]1[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[S:3][CH2:2][N:16]1[CH:17]=[C:12]([Cl:11])[CH:13]=[N:14][C:15]1=[O:18]

Participants

5

Reactant 3

HCID 11658340HCID 11658340, compoundHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 20161345HCID 20161345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

2-Chloromethylsulfenyl-1-methylimidazole [see Preparation 10] (10 mmol) in DMF (12 ml) was added to a mixture of 5-chloropyrimidin-2-one hydrochloride (10 mmol) and potassium tert-butoxide (20 mmol) in DMF (72 ml). The mixture was stirred at 60° C. for 51/2 hours before the product was distilled off and the residue washed with water and ether. The product was oily. 1H HMR (DMSO d6, δ): 3.57 (CH3), 5.27 (--CH2 --), 6.95-7.22 (imidazole), 8.19 (H-4, d, j 4 Hz), 8.54 (H-6, d, J 4 Hz).

Workup

  1. distillationwas distilled off
  2. washthe residue washed with water and ether

Sources & evidence

ORD record
ord-503810812fc843928b819006f9a6d04c
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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