HCID 178499068, compound → HCID 178513787, compound

HRID 2428028Notes

Reaction equation

HRID 2428028 reaction equation
C[O:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[NH:16][C:15]3[C:10]2=[N:11][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][Si](C(C)C)(C(C)C)C(C)C)[CH:24]=2)=[N:13][C:14]=3[C:19]([O:21]C)=O)[CH2:5][CH2:4]1.[NH2:40]C1C(C(OC)=O)=NC(C2C=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=2)=NC=1N[C@H]1CC[C@@H](OC)CC1>ClCCl>[OH:2][C@@H:3]1[CH2:4][CH2:5][C@H:6]([N:9]2[C:17](=[O:18])[NH:16][C:15]3[C:10]2=[N:11][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)=[N:13][C:14]=3[C:19]([NH2:40])=[O:21])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 178499068HCID 178499068, compoundHCID 178499070HCID 178499070, compound

Product 1

HCID 178513787HCID 178513787, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 9-(cis-4-methoxycyclohexyl)-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 5-amino-6-(cis-4-methoxycyclohexylamino)-2-(3-(triisopropylsilyloxy)phenyl)pyrimidine-4-carboxylate (0.223 g, 0.422 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.547 g, 3.38 mmol) in dichloromethane (20 mL) were reacted according to General Procedure F and purified using biotage chromatography (0 to 65% EtOAc in hexanes) to afford the title compound (0.210 g, 90%). MS (ESI) m/z 555.5 [M+1]+.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-c7c2ad68cb1d419da7a82171b1fa08e1
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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