Dimethylformamide → HCID 86663389, compound

HRID 421319Notes

Reaction equation

HRID 421319 reaction equation
[Cl:1]N1C(=O)CCC1=O.CN(C)C=O.[CH:14]1([CH2:17][N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21]([C:33]2[CH:34]=[N:35][C:36]([CH2:39][NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[N:37][CH:38]=2)=[N:22][C:23]=3[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:16][CH2:15]1>C(OCC)(=O)C>[Cl:1][C:26]1[N:18]([CH2:17][CH:14]2[CH2:16][CH2:15]2)[C:19]2[C:24]([N:25]=1)=[C:23]([N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)[N:22]=[C:21]([C:33]1[CH:38]=[N:37][C:36]([CH2:39][NH:40][C:41](=[O:47])[O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[N:35][CH:34]=1)[N:20]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398Chlorosuccinimide2×HCID 86663388HCID 86663388, compound

Product 1

HCID 86663389HCID 86663389, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-Chlorosuccinimide (0.92 g, 6.89 mmol) was added to an N,N-dimethylformamide solution (60 ml) of tert-butyl {5-[9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-yl}methylcarbamate (2.14 g, 4.59 mmol) at room temperature. The resulting mixture was stirred for 4.5 hours followed by the addition of N-chlorosuccinimide (0.12 g, 0.92 mmol) and the resulting mixture was further stirred for 2.5 hours. The reaction mixture was poured into ethyl acetate, 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 silica gel column chromatography (hexane:ethyl acetate=17:3 to 3:1) to give the title compound (1.29 g, 56%, two steps combined) as a colorless amorphous substance.

Workup

  1. stirringthe resulting mixture was further stirred for 2.5 hours
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=17:3 to 3:1)

Sources & evidence

ORD record
ord-0a158b74ed5f49c69c081900143ed8c6
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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