1,1'-Carbonyldiimidazole → HCID 24937986, compound

HRID 391625Notes

Reaction equation

HRID 391625 reaction equation
[CH:1]1([N:6]2[C:14](=[O:15])[NH:13][C:12]3[C:7]2=[N:8][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[N:10][C:11]=3[C:16]([O:18]CC)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:28]C1C(C(OCC)=O)=NC(C2C=CC=C(O)C=2)=NC=1NC1CCCC1.C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[CH:1]1([N:6]2[C:14](=[O:15])[NH:13][C:12]3[C:7]2=[N:8][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[N:10][C:11]=3[C:16]([NH2:28])=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 57474583HCID 57474583, compoundHCID 57474584HCID 57474584, compound

Product 1

HCID 24937986HCID 24937986, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 9-cyclopentyl-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-6-(cyclopentylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate (76.3 mg, 0.223 mmol) was dissolved in methylene chloride (5 ml) and 1,1′-carbonyldiimidazole (361.6 mg, 2.23 mmol) was added. The reaction was refluxed for 1H and then stirred at room temperature for 5 days. The solvent was removed under reduced pressure and the crude material was purified by column chromatography (50% ethyl acetate in hexanes) to provide the title compound (49.7 mg, 0.135 mmol, 60% yield). MS (ESI) m/z 369.4 [M+1]+.

Workup

  1. temperatureThe reaction was refluxed for 1H
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material was purified by column chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c06b697d09a541fcbcf17168a7cc539c
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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