Ammonia → tert-butyl (2R)-2-{[(7-methoxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate

HRID 640015Notes

Reaction equation

HRID 640015 reaction equation
CC(C)(C)C(OC[N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([O:32][CH3:33])=[CH:13][C:14]=2[O:18][CH2:19][C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[N:9]=[CH:8]1)=O.N>CO>[CH3:33][O:32][C:12]1[CH:11]=[C:10]2[C:15]([C:16](=[O:17])[NH:7][CH:8]=[N:9]2)=[C:14]([O:18][CH2:19][C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86609388tert-butyl (2R)-2-{[(3-{[(2,2-dimethylpropanoyl)oxy]methyl}-7-methoxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate

Product 1

HCID 136383491tert-butyl (2R)-2-{[(7-methoxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl (2R)-2-{[(3-{[(2,2-dimethylpropanoyl)oxy]methyl}-7-methoxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate (0.750 g, 1.5 mmol) was stirred in a 7N solution of ammonia in methanol (250 ml) at room temperature for 24 hours. The mixture was evaporated under reduced pressure to give tert-butyl (2R)-2-{[(7-methoxy-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate (0.560 g, 100% yield) which was used in the next stage without further purification.

Workup

  1. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c93826f0a27b4a0186f59b77d5aa72eb
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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