Dimethyl Sulfoxide → HCID 59333644, compound

HRID 1876494Notes

Reaction equation

HRID 1876494 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, compoundYield 79%

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. The organic layer was dried over anhydrous sodium sulfate, the reaction mixture was filtrated, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=20:1) to give the title compound (120.5 mg, 79%) as a pale yellow solid.

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
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationthe reaction mixture was filtrated
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-a58436e76a65488bbb216dd90d7dc680
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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