Water → HCID 67211772, compound

HRID 2068584Notes

Reaction equation

HRID 2068584 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[N:12][C:13](Cl)=[N:14][C:15]=2[NH2:17])[N:10]=[CH:9]1)([CH3:4])[CH3:3].[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.O.C(OCC)(=O)C>CS(C)=O>[C:29]([O:28][C:26]([N:20]1[CH2:25][CH2:24][N:23]([C:13]2[N:12]=[C:11]3[C:16]([N:8]([CH2:7][C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:19])[CH:9]=[N:10]3)=[C:15]([NH2:17])[N:14]=2)[CH2:22][CH2:21]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86639988HCID 86639988, compound2×

Product 1

HCID 67211772HCID 67211772, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred mixture of (6-amino-2-chloro-purin-7-yl)-acetic acid 1,1-dimethylethyl ester, 3 (5 g, 17.6 mmol) in dimethylsulfoxide (50 ml) was added tert-butyl piperazine-1-carboxylate (10 g, 53.8 mmol) at 120° C. After the addition, the mixture was stirred for about 14 h. Water (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture. The organic layers was then washed with H2O several times, dried with Na2SO4 and concentrated to give crude product 4-(6-amino-7-tert-butoxycarbonylmethyl-7H-purin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester, 4 (7 g) which was not purified and used for the next reaction directly.

Workup

  1. additionAfter the addition
  2. washThe organic layers was then washed with H2O several times
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be69e92598af41e48b611879d00b6c7b
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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