Piperazine → 5-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876624Notes

Reaction equation

HRID 1876624 reaction equation
Cl[C:2]1[N:3]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]1[CH3:17])[N:7]=[C:6]([C:18]1[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=1)[N:5]=2.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CN1CCCC1=O>[CH2:25]([N:3]1[C:2]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[N:10][C:9]2[C:4]1=[N:5][C:6]([C:18]1[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=1)=[N:7][C:8]=2[N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]1[CH3:17])[CH:26]([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 593335215-{8-chloro-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-2-yl}pyrimidin-2-amine

Product 1

HCID 593335555-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amineYield 71.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

An N-methyl-2-pyrrolidone (2 ml) solution of 5-{8-chloro-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-2-yl}pyrimidin-2-amine (307 mg, 0.76 mmol) and piperazine (328 mg, 3.81 mmol) was stirred at 150° C. for 90 minutes and returned to room temperature. The reaction mixture was purified by flash silica gel column chromatography (chloroform:methanol=95:5 to 85:15) to give the title compound (245 mg, 71%) as a solid.

Workup

  1. customreturned to room temperature
  2. customThe reaction mixture was purified by flash silica gel column chromatography (chloroform:methanol=95:5 to 85:15)

Sources & evidence

ORD record
ord-9f54d034f9fc4af98423aafa7be026c7
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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