Trimethyl orthoformate → HCID 70798266, compound

HRID 1363141Notes

Reaction equation

HRID 1363141 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:15]=1[CH2:16][N:17]1[C:25](=[O:26])[N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]2[C:18]1=[N:19][C:20]([NH:34][C:35]1[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:36]=1[NH2:43])=[N:21][CH:22]=2.C(OC)(OC)OC>CO>[F:13][C:14]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:15]=1[CH2:16][N:17]1[C:25](=[O:26])[N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]2[C:18]1=[N:19][C:20]([N:34]1[C:35]3[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:36]=3[N:43]=[CH:2]1)=[N:21][CH:22]=2

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 59727008HCID 59727008, compound

Product 1

HCID 70798266HCID 70798266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A catalytic amount of para-toluene sulfonic acid monohydrate was added to a solution of the above amine intermediate and trimethyl orthoformate (3 mL) in MeOH (10 mL). After 1 hr the crude material was adsorbed onto silica gel and purified by column chromatography (eluted with 1 and 2% MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(6-cyano-1H-benzo[d]imidazol-1-yl)-8-oxo-8,9-dihydropurine-7-carboxylate (60) (164 mg), MH+=504 and MH+-BOC=404.

Workup

  1. custompurified by column chromatography (eluted with 1 and 2% MeOH/DCM)

Sources & evidence

ORD record
ord-3b0a8481dca04de9ae6c896509acac66
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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