2-(Benzenesulfonyl)-3-phenyloxaziridine → 4-(Isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide

HRID 2280777ノート

反応式

HRID 2280777 の反応式
[CH:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2].C1(C2[O:24]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([S:14]([CH3:15])=[O:24])[N:6]=1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridine2 回HCID 709813214-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide

生成物 1

HCID 709812914-(Isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide収率 92.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirring solution of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide (170 g, 0.751 mol) in chloroform (22 L) was added portion-wise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (235.6 g, 0.902 mol) and the resulting solution was stirred at ambient temperature overnight. An additional amount of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (19.6 g, 0.075 mol) was added and the mixture was then stirred overnight at ambient temperature. The reaction solution was concentrated under reduced pressure to give the crude product as a white solid. The solids were triturated with ethyl acetate (1.5 L) at ambient temperature for 1 h, filtered, washed with ethyl acetate (250 mL), and dried in a vacuum oven overnight at 45° C. to afford 4-(isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide (167.7 g, 92% yield) as white solid. MS (ESI) m/z 243.2 [M+1]+.

後処理

  1. stirringthe mixture was then stirred overnight at ambient temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customto give the crude product as a white solid
  4. customThe solids were triturated with ethyl acetate (1.5 L) at ambient temperature for 1 h
  5. filtrationfiltered
  6. washwashed with ethyl acetate (250 mL)
  7. customdried in a vacuum oven overnight at 45° C.

出典と根拠

ORDレコード
ord-b0f959d0033e447dad6775d73bb3ceef
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

反応ノート

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