5-Chloro-2(1H)-pyrimidinone → 1(4-Chlorophenylsulfinyl)methyl-5-chloropyrimidin-2-one

HRID 247066Notes

Reaction equation

HRID 247066 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[N:10][C:11](=[O:14])[NH:12][CH:13]=1.Br[CH2:16][S:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[O:18]>CN(C=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([S:17]([CH2:16][N:10]2[CH:9]=[C:8]([Cl:7])[CH:13]=[N:12][C:11]2=[O:14])=[O:18])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 156504781-Bromomethylsulfinyl-4-chlorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 156504871(4-Chlorophenylsulfinyl)methyl-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium tert-butoxide (4 mmol) in DMF (10 ml) was added to a solution of 5-chloropyrimidin-2-one (4 mmol) in DMF (40 ml). The mixture was stirred at room temperature for 10 min before 1-bromomethylsulfinyl-4-chlorobenzene (see Preparation 5) (4 mmol) was added. The resultant mixture was stirred at 60° C. for 2 days, the solvent distilled off at reduced pressure, the residue triturated with water, the insoluble material dried and washed with a little chloroform before recrystallization from DMSO; the crystalline material was also washed with a little methanol and finally with water; yield 0.30 g (25%), m.p. 262° C. (Found: C43.63; H2.68. Calc. for C11H8Cl2N2O2S: C43.59; H2.67)1H NMR (DMSO-d6): δ 5.12 (CH2), 7.60 (Ph, b.s.), 8.19 and 8.62 (H-4, H-6, d, J 4 Hz). IR (KBr): 1660 (CO), 1060 cm-1 (SO) MS (70 eV; m/e (rel int. %): 302 (0.5, M), 159 (6), 145 (33), 143 (100).

Workup

  1. additionwas added
  2. distillationthe solvent distilled off at reduced pressure
  3. customthe residue triturated with water
  4. customthe insoluble material dried
  5. washwashed with a little chloroform before recrystallization from DMSO
  6. washthe crystalline material was also washed with a little methanol and finally with water

Sources & evidence

ORD record
ord-2f1f4169d0d94097aa2e39cb3be2c552
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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