Ammonium Hydroxide → HCID 178453129, compound

HRID 1504074Notes

Reaction equation

HRID 1504074 reaction equation
C(=O)(OC(C)(C)C)[O:2][C:3]1[C:4]2[CH:11]=[C:10]([CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.[NH4+].[OH-]>CO>[OH:2][C:3]1[C:4]2[CH:11]=[C:10]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[S:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86695233HCID 86695233, compound

Product 1

HCID 178453129HCID 178453129, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 25-mL round-bottom flask containing a solution of 6-(2-[[(tert-butoxy)carbonyl]amino]ethyl)thieno[2,3-d]pyrimidin-4-yl tert-butyl carbonate (370 mg, 0.94 mmol, 1.00 equiv) in 10 mL of methanol was added NH4OH (2.1 mL) at room temperature and the resulting solution was stirred for 2 hours under N2. After completion, the resulting mixture was concentrated under vacuum and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to afford 252 mg (91%) of the desired tert-butyl N-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate as a white solid. MS (ES): m/z 296 (M+H)+.

Workup

  1. concentrationAfter completion, the resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-f7fedced1a7f44b884a3751278175272
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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