HCID 178470293, compound → HCID 178489572, compound

HRID 391655Notes

Reaction equation

HRID 391655 reaction equation
[N:1]1([C:6]([O:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16]3[N:24]=[C:23]4[C:19]([NH:20][C:21](=[O:33])[N:22]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[O:31][CH3:32])=[C:18]([C:34]([O:36]CC)=O)[N:17]=3)[CH2:11][CH2:10]2)=[O:7])C=CN=C1.[NH2:39]C1C(C(OCC)=O)=NC(N[C@H]2CC[C@@H](O)CC2)=NC=1NC1C=CC=CC=1OC>ClCCl>[C:6](=[O:7])([O:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([NH:15][C:16]2[N:24]=[C:23]3[C:19]([NH:20][C:21](=[O:33])[N:22]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])=[C:18]([C:34](=[O:36])[NH2:39])[N:17]=2)[CH2:13][CH2:14]1)[NH2:1]

Participants

4

Reactant 2

HCID 178470293HCID 178470293, compoundHCID 178470297HCID 178470297, compound

Product 1

HCID 178489572HCID 178489572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(cis-4-(1H-imidazole-1-carbonyloxy)cyclohexylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-2-(cis-4-hydroxycyclohexylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (0.272 g, 0.678 mmol) and 1,1′-1,1′-carbonyldiimidazole (1.09 g, 6.78 mmol) in dichloromethane (20 mL) were reacted according to General Procedure F and purified using biotage chromatography (60-100% ethyl acetate in hexanes) to afford the title compound and the free hydroxyl derivative (0.250 g, 71%). MS (ESI) m/z 522.4 [M+1]+.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-2c5f94b018c945328151b49eb615369a
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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