(R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one → 2-(tert-butylamino)-3-methyl-8-(4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinone

HRID 1056294Notes

Reaction equation

HRID 1056294 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[C:8](=[C:9](I)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].C[C@@H:20]1[C:24]2[NH:25][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:23]=2[C:22](=[O:37])[NH:21]1>>[C:1]([NH:5][C:6]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[C:8](=[C:9]([C:26]3[NH:25][C:24]4[CH2:20][NH:21][C:22](=[O:37])[C:23]=4[CH:27]=3)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89781988(R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-oneHCID 897821382-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one

Product 1

HCID 897837012-(tert-butylamino)-3-methyl-8-(4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinoneYield 19%

Procedure

This compound (54 mg, 0.15 mmol, 19% yield) as a tan solid was prepared according to the procedures described for Example 287, using 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one (701; 281 mg, 0.79 mmol), and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (706; 477 mg, 1.35 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.10 (s, 1H), 7.84-7.93 (m, 1H), 7.51 (s, 1H), 7.18 (t, J=7.73 Hz, 1H), 6.80 (d, J=1.56 Hz, 1H), 5.96 (s, 1H), 4.25 (d, J=0.59 Hz, 2H), 3.48 (s, 3H), 1.51 (s, 9H). m/z (ESI, +ve) 325.1 (M+H).

Sources & evidence

ORD record
ord-56e6786285aa4ced80f4abc4e14417be
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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