Trifluoroacetic acid → 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-methylquinazolin-4(3H)-one

HRID 77386Notes

Reaction equation

HRID 77386 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:13]3[CH2:17][CH:16]4[CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][CH:15]4[CH2:14]3)[CH:9]=2)[N:4]=[CH:3]1.FC(F)(F)C(O)=O>ClCCl.CO>[CH2:14]1[CH:15]2[CH2:20][NH:19][CH2:18][CH:16]2[CH2:17][N:13]1[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[CH:3][N:2]([CH3:1])[C:11]2=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69928551tert-butyl 5-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate2×

Product 1

HCID 699282016-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-methylquinazolin-4(3H)-oneYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (Intermediate 20A) (80 mg, 0.22 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.5 mL) and the reaction allowed to stand overnight. The reaction was diluted with methanol and passed through a scx cartridge (500 mg) to afford 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-methylquinazolin-4(3H)-one (58 mg, 0.21 mmol).

Sources & evidence

ORD record
ord-6775547a2bcf4d0eabae6ed7e8d29aad
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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