5-Chloropyrimidin-2-ol hydrochloride → 1-(4-Chlorophenylsulfenyl)methyl-5-chloropyrimidin-2-one

HRID 247065

反応式

HRID 247065 の反応式
CC(C)([O-])C.[K+].Cl.[Cl:8][C:9]1[CH:10]=[N:11][C:12](=[O:15])[NH:13][CH:14]=1.Br[CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1>CN(C=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([S:18][CH2:17][N:11]2[CH:10]=[C:9]([Cl:8])[CH:14]=[N:13][C:12]2=[O:15])=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 135300861-Bromomethylthio-4-chlorobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 42952761-(4-Chlorophenylsulfenyl)methyl-5-chloropyrimidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Potassium tert-butoxide (40 mmol) in DMF (25 ml) was added to a solution of 5-chloropyrimidin-2-one hydrochloride (20 mmol) in DMF (125 ml). The mixture was stirred at room temperature for 15 min before 1-bromomethylsulfenyl-4-chlorobenzene [see U.S. Pat. No. 2,827,492; Chem. Abstract 52 Pl 6296 d (1958)] (25 mmol) was added. The resultant mixture was stirred at room temperature at 60° C. for 3h, the solvent removed at reduced pressure and the residue triturated with water and dried. The residual product was a mixture of the N- and O-alkylated isomers in the ratio 3:1 (1H NMR); yield 4.2 g (73%). The isomers were separated by their different solubilities in acetone, the less polar O-isomer being the more soluble isomer. The title compound, the N- isomer had m.p. 191° C. (acetone). (Found C45.90; H2.78. Calc. for C11H8Cl2N2OS: C46.00; H2.81) 1H NMR (CDCl3): δ 5.25 (CH2), 7.35 (Ph, s), 8.20 and 8.50 (H-4, H-6, d, J 4Hz). IR (KBr): 1660 cm-1 (CO). MS (70 eV; m/z (% rel. int)): 286 (4, M), 157 (11), 156 (11), 145 (33), 143 (100), 116 (27).

後処理

  1. additionAbstract 52 Pl 6296 d (1958)] (25 mmol) was added
  2. customthe solvent removed at reduced pressure
  3. customthe residue triturated with water
  4. customdried
  5. additiona mixture of the N- and O-alkylated isomers in the ratio 3:1 (1H NMR)
  6. customThe isomers were separated by their different solubilities in acetone

出典と根拠

ORDレコード
ord-35673b92983440ec82c97c089d764d70
出典データセット
uspto-grants-1987_11
特許番号
US04705791

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