Water → HCID 68525216, compound

HRID 1989800Notes

Reaction equation

HRID 1989800 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)=[O:12])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:25])[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl[C:34]([O:36]CC)=[O:35].O>C(Cl)Cl>[CH2:11]([O:12][C:34](=[O:35])[OH:36])[CH3:9].[NH2:1][C:2]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)=[O:12])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:25])[N:6]2[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11977601HCID 11977601, compound

Product 1

HCID 68525216HCID 68525216, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-N-(cyclopropylmethyl)-8-oxo-8,9-dihydro-7H-purine-2-carboxamide (Example 1, 50 mg, 0.15 mmol) was taken up in 2 ml DCM under a nitrogen atmosphere at room temperature and firstly triethylamine (62 μl, 0.44 mmol) and then ethyl chloroformate (28 μl, 0.30 mmol) were added in one portion each and the whole stirred at room temperature for 4 h. The mixture was poured into water (5 ml) and extracted with DCM (3×2 ml). The combined organics were dried over MgSO4 and concentrated in vacuo to a yellow residue which was purified by column chromatography using a gradient of 1:1 DCM:EtOAc→EtOAc as the eluant. Combination and evaporation of the appropriate fractions provided the title compound as a white solid (20 mg).

Workup

  1. extractionextracted with DCM (3×2 ml)
  2. dry with materialThe combined organics were dried over MgSO4
  3. concentrationconcentrated in vacuo to a yellow residue which
  4. customwas purified by column chromatography
  5. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-a85993dd6e7e40c9a20bcdc532440fd2
Source dataset
uspto-grants-2010_01
Patent number
US07642350B2

Reaction notes

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