(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-(2-methoxyethyl)-8-(4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinone

HRID 1056332Notes

Reaction equation

HRID 1056332 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:20])[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:23]1[C:27]2[NH:28][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:30][C:26]=2[C:25](=[O:40])[NH:24]1>>[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:20])[C:13]2[C:8](=[C:9]([C:29]3[NH:28][C:27]4[CH2:23][NH:24][C:25](=[O:40])[C:26]=4[CH:30]=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 897820952-(tert-butylamino)-8-iodo-3-(2-methoxyethyl)quinazolin-4(3H)-one

Product 1

HCID 897833422-(tert-butylamino)-3-(2-methoxyethyl)-8-(4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinoneYield 51.3%

Procedure

This compound (138 mg, 51% yield) as a brown solid was prepared according to the procedure described for Example 448, using 2-(tert-butylamino)-8-iodo-3-(2-methoxyethyl)quinazolin-4(3H)-one (715) (273 mg, 0.68 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) (219 mg, 0.88 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (1H, br.), 7.90 (2H, m), 7.56 (1H, br.), 7.20 (1H, t, J=7.4 Hz), 6.83 (1H, s), 6.50 (1H, s), 4.27 (4H, m), 3.70 (2H, m), 3.35 (3H, s), 1.49 (9H, s). m/z (ESI, +ve) 395.9 (M+H)+.

Sources & evidence

ORD record
ord-2180a1b3fa1142718576a7ce9ff14d24
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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