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

HRID 1876591

Reaction equation

HRID 1876591 reaction equation
C(N(CC)CC)C.C(Cl)Cl.[CH:11]1([CH2:14][N:15]2[C:23]([N:24]3[CH2:29][CH2:28][NH:27][C@H:26]([CH3:30])[CH2:25]3)=[N:22][C:21]3[C:16]2=[N:17][C:18]([C:37]2[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=2)=[N:19][C:20]=3[N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH2:13][CH2:12]1.[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]([CH2:14][CH:11]3[CH2:13][CH2:12]3)[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 593335225-{9-(cyclopropylmethyl)-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

Product 1

HCID 593336595-{8-[(3R)-4-Acetyl-3-methylpiperazin-1-yl]-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amineYield 100.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Triethylamine (77.3 μl, 0.55 mmol) was added to a methylene chloride solution (3.0 ml) of 5-{9-(cyclopropylmethyl)-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (104.1 mg, 0.23 mmol) at room temperature followed by the addition of acetic anhydride (26.2 μl, 0.28 mmol) with ice cooling. The resulting mixture was stirred at room temperature for 95 minutes and the reaction mixture was poured into methylene chloride-methanol (10:1), washed with water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 16:1) to give the title compound (114.3 mg, 100%) as a pale yellow solid.

Workup

  1. washwashed with water
  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 medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 16:1)

Sources & evidence

ORD record
ord-3b02dc2e58754925b901fef4e75849ef
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Linked notes

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