Dichloromethane → 5-{8-[(3R)-4-Acetyl-3-methylpiperazin-1-yl]-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876593Notes

Reaction equation

HRID 1876593 reaction equation
C(N(CC)CC)C.C(Cl)Cl.[CH2:11]([N:15]1[C:23]([N:24]2[CH2:29][CH2:28][NH:27][C@H:26]([CH3:30])[CH2:25]2)=[N:22][C:21]2[C:16]1=[N:17][C:18]([C:37]1[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=1)=[N:19][C:20]=2[N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH:12]([CH3:14])[CH3:13].[C:44](OC(=O)C)(=[O:46])[CH3:45]>C(Cl)Cl.CO>[C:44]([N:27]1[CH2:28][CH2:29][N:24]([C:23]2[N:15]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:16]3[C:21]([N:22]=2)=[C:20]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:19]=[C:18]([C:37]2[CH:42]=[N:41][C:40]([NH2:43])=[N:39][CH:38]=2)[N:17]=3)[CH2:25][C@H:26]1[CH3:30])(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 593335435-{9-Isobutyl-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

Product 1

HCID 593336475-{8-[(3R)-4-Acetyl-3-methylpiperazin-1-yl]-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amineYield 94%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Triethylamine (79.9 μl, 0.57 mmol) was added to a methylene chloride solution (3.0 ml) of 5-{9-isobutyl-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (108.1 mg, 0.24 mmol) at room temperature followed by the addition of acetic anhydride (27.1 μl, 0.29 mmol) with ice cooling. The resulting mixture was stirred at room temperature for 1 hour and then the reaction mixture was poured into methylene chloride-methanol (10:1), washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to give the title compound (110.9 mg, 94%) as a pale yellow solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-2330394ec26147a2a117e7771a0f0555
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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