Sodium Hydroxide → 5-(Tert-butyl)-2-(5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamino)furan-3-carbonitrile

HRID 1529823Notes

Reaction equation

HRID 1529823 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[Se:10][C:6]=2[N:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[O:17][C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][C:20]=1[C:21]#[N:22].[OH-].[Na+]>CN(C=O)C>[C:23]([C:18]1[O:17][C:16]([NH:15][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[Se:10][C:6]=3[N:5]=[CH:4][N:3]=2)=[C:20]([C:21]#[N:22])[CH:19]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 696716892-Amino-5-tert-butylfuran-3-carbonitrileHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 573773125-(Tert-butyl)-2-(5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamino)furan-3-carbonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (500 mg, 1.83 mmol, from step b of example 1) in DMF (15 mL) was added sequentially 2-amino-5-tert-butylfuran-3-carbonitrile (300 mg, 1.83 mmol) and powdered NaOH (210 mg, 5.49 mmol) at rt. Work-up as described in example 2, gave the product as a yellow color solid (400 mg, 55%), mp 230-232° C. 1H NMR (400 MHz, CDCl3): δ 9.78 (1H, s, H-2), 6.94 (1H, br s, exchangeable with D2O, —NH), 6.35 (1H, s, H-4′), 3.30-3.31 (2H, m, H-8), 2.95 (2H, br s, H-5), 1.90-1.92 (4H, m, H-6,7), 1.38 (9H, s, tert-butyl); 13C NMR (100 MHz, CDCl3): δ 163.2, 161.7, 158.0, 154.0, 144.7, 142.9, 137.1, 133.8, 125.9, 101.4, 97.8, 33.0, 29.0, 28.8, 28.4, 23.1, 22.5; LC-MS (positive ion mode): m/z 399, 401 (M+H)+.

Sources & evidence

ORD record
ord-1863d792e58648e3bfba0188ae27e195
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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