HCID 178470189, compound → HCID 178513786, compound

HRID 391710Notes

Reaction equation

HRID 391710 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:23](=[O:24])[NH:22][C:21]3[C:16]2=[N:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)=[N:19][C:20]=3[C:25]([O:27]CC)=O)[CH2:11][CH2:10]1)=O)(C)(C)C.[NH2:37]C1C(C(OCC)=O)=NC(C2C=CC=C(O)C=2)=NC=1N[C@H]1CC[C@H](NC(OC(C)(C)C)=O)CC1>ClCCl>[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:23](=[O:24])[NH:22][C:21]3[C:16]2=[N:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)=[N:19][C:20]=3[C:25]([NH2:37])=[O:27])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 178470189HCID 178470189, compoundHCID 178470190HCID 178470190, compound

Product 1

HCID 178513786HCID 178513786, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 9-(trans-4-(tert-butoxycarbonylamino)cyclohexyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-6-(trans-4-(tert-butoxycarbonylamino)cyclohexylamino)-2-(3-hydroxyphenyl)pyrimidine-4-carboxylate (0.150 g, 0.317 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.514 g, 3.17 mmol) in dichloromethane (10 mL) were reacted according to General Procedure F and purified via biotage chromatography (0 to 60% EtOAc in hexanes) to afford the title compound (0.070 g, 44%). MS (ESI) m/z 498[M+1]+.

Workup

  1. custompurified via biotage chromatography (0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-051cbd125b5f4ee9a60c267ca20e340e
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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