m-Chloroperbenzoic acid → 4-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylsulfinylpyrimidine

HRID 917631Notes

Reaction equation

HRID 917631 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N:17]2[CH2:22][CH2:21][N:20]3[CH:23]=[CH:24][N:25]=[C:19]3[CH2:18]2)[N:10]=[C:9]([S:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]=1.ClC1C=CC=C(C(OO)=[O:47])C=1>C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N:17]2[CH2:22][CH2:21][N:20]3[CH:23]=[CH:24][N:25]=[C:19]3[CH2:18]2)[N:10]=[C:9]([S:26]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:47])[N:8]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178483034-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylthiopyrimidine

Product 1

HCID 178483024-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylsulfinylpyrimidine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a chloroform solution 2 ml of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylthiopyrimidine (prepared in the above (4)) 104 mg is dropped a solution of m-chloroperbenzoic acid 43 mg in chloroform 3 ml over a period of 20 minutes on an ice bath, and the mixture is stirred for 1 hour. The reaction mixture is diluted with an aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylsulfinylpyrimidine as a slightly yellow caramel.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0987e39112364939b837d88a5661b95d
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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