Dimethyl Sulfoxide → HCID 59333644, compound

HRID 421304Notes

Reaction equation

HRID 421304 reaction equation
CS(C)=O.Cl[C:6]1[N:7]([CH2:29][CH:30]2[CH2:32][CH2:31]2)[C:8]2[C:13]([N:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:11]=[C:10]([C:21]1[CH:22]=[N:23][C:24]([NH:27][CH3:28])=[N:25][CH:26]=1)[N:9]=2.[S:33]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:36])(=[O:35])=[O:34]>ClCCl.CO>[CH:30]1([CH2:29][N:7]2[C:6]([N:40]3[CH2:41][CH2:42][N:37]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:38][CH2:39]3)=[N:14][C:13]3[C:8]2=[N:9][C:10]([C:21]2[CH:22]=[N:23][C:24]([NH:27][CH3:28])=[N:25][CH:26]=2)=[N:11][C:12]=3[N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7091611-(Methylsulfonyl)piperazine2×HCID 59333551HCID 59333551, compound

Product 1

HCID 59333644HCID 59333644, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A dimethyl sulfoxide solution (1.0 ml) of 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-N-methylpyrimidin-2-amine (140.5 mg, 0.29 mmol) and N-mesylpiperazine (190.2 mg, 1.16 mmol) was heated at 140° C. and stirred for 3 hours. N-Mesylpiperazine (190.2 mg, 1.16 mmol) was added, the resulting mixture was further stirred for 5.5 hours and left standing to cool followed by the addition of dichloromethane-methanol (10:1), and the resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution.

Workup

  1. stirringthe resulting mixture was further stirred for 5.5 hours
  2. waitleft
  3. temperatureto cool
  4. washthe resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution

Sources & evidence

ORD record
ord-f96c8f80baf046f593899d01ec06dbbf
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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