Triethylamine → 4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-N,N-dimethylpiperazine-1-carboxamide

HRID 1876542Notes

Reaction equation

HRID 1876542 reaction equation
C(N(CC)CC)C.[CH2:8]([N:12]1[C:20]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[N:19][C:18]2[C:13]1=[N:14][C:15]([C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[N:37][CH:38]=1)=[N:16][C:17]=2[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[CH:9]([CH3:11])[CH3:10].[CH3:40][N:41]1[CH2:45]CC[C:42]1=[O:46]>>[NH2:39][C:36]1[N:37]=[CH:38][C:33]([C:15]2[N:14]=[C:13]3[C:18]([N:19]=[C:20]([N:21]4[CH2:26][CH2:25][N:24]([C:42]([N:41]([CH3:45])[CH3:40])=[O:46])[CH2:23][CH2:22]4)[N:12]3[CH2:8][CH:9]([CH3:11])[CH3:10])=[C:17]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:16]=2)=[CH:34][N:35]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 593335015-(9-Isobutyl-6-morpholino-8-(piperazin-1-yl)-9H-purin-2-yl)pyrimidin-2-amine

Product 1

HCID 593336134-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-N,N-dimethylpiperazine-1-carboxamideYield 43%

Procedure

Triethylamine (64 μl) and 2-acetamide-4-dimethylcarbamoyl chloride (35 μl) were added to an N-methylpyrrolidone solution (1 ml) of 5-(9-isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-ylamine (100 mg) and the resulting mixture was stirred for 24 hours. The reaction mixture was partitioned with ethyl acetate and water, the insoluble solid was collected by filtration, and then the organic layer of the filtrate was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was combined with the solid separately collected by filtration followed by the addition of dimethyl sulfoxide (3 ml) and water (3 ml), the resulting mixture was stirred, and the insoluble matter was collected by filtration, washed with water, and dried to give the title compound (50 mg, 43%) as a pale yellow solid.

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. filtrationthe insoluble solid was collected by filtration
  3. dry with materialthe organic layer of the filtrate was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationseparately collected by filtration
  6. additionfollowed by the addition of dimethyl sulfoxide (3 ml) and water (3 ml)
  7. stirringthe resulting mixture was stirred
  8. filtrationthe insoluble matter was collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-38b130b8bbbc41ca8b0a8ad7be3a0fe5
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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