4-Methylmorpholine → 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl (4-nitrophenyl) carbonate

HRID 51515Notes

Reaction equation

HRID 51515 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10].[NH2:21][C:22]1[C:23]2[C:30]([C:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:33][CH:32]=3)=[CH:29][N:28]([CH:44]3[CH2:48][CH2:47][CH:46]([OH:49])[CH2:45]3)[C:24]=2[N:25]=[CH:26][N:27]=1>ClCCl>[C:9](=[O:10])([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)[O:49][CH:46]1[CH2:47][CH2:48][CH:44]([N:28]2[C:24]3[N:25]=[CH:26][N:27]=[C:22]([NH2:21])[C:23]=3[C:30]([C:31]3[CH:32]=[CH:33][C:34]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:35][CH:36]=3)=[CH:29]2)[CH2:45]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 227362353-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentan-1-ol

Product 1

HCID 865890083-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl (4-nitrophenyl) carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Methylmorpholine (0.007 ml, 0.062 mmol) was added dropwise to solution of 4-nitrophenyl chloroformate (12.5 mg, 0.062 mmol) in dichloromethane (1 ml) with stirring under nitrogen at 0° C. After 20 minutes, the ice-water bath was removed and the mixture was allowed to warm up to ambient temperature. 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentanol (20 mg, 0.052 mmol) was added to the mixture and the resulting solution was stirred for 24 hours. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium bicarbonate, and brine. The organic layer was dried (MgSO4), filtered and evaporated to give 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl (4-nitrophenyl) carbonate. The structure was confirmed by 1H NMR.

Workup

  1. customthe ice-water bath was removed
  2. temperatureto warm up to ambient temperature
  3. stirringthe resulting solution was stirred for 24 hours
  4. washwashed with water, saturated sodium bicarbonate, and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c388fc5ca90544aa9cab944ac31c5aea
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

Loading…