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

HRID 1529824Notes

Reaction equation

HRID 1529824 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]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:20]=1[C:21]#[N:22].[OH-].[Na+]>CN(C=O)C>[C:23]1([C:18]2[O:17][C:16]([NH:15][C:2]3[C:7]4[C:8]5[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=5[Se:10][C:6]=4[N:5]=[CH:4][N:3]=3)=[C:20]([C:21]#[N:22])[CH:19]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6939612-Amino-5-phenylfuran-3-carbonitrileHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 573773135-Phenyl-2-(5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamino)furan-3-carbonitrileYield 78%

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 (250 mg, 0.917 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 2-amino-5-phenylfuran-3-carbonitrile (160 mg, 0.917 mmol; Matsuda, T.; Yamagata, K.; Tomioka, Y.; Yamazaki, M. Chem. Pharm. Bull., 1985, 33, 937-943) and powdered NaOH (110 mg, 2.751 mmol) at rt. Work-up as described in example 2, gave the product as a yellow color solid (300 mg, 78%), mp 252-256° C. (decomp). 1H NMR (400 MHz, CDCl3): δ 9.82 (1H, s, H-2), 7.78-7.81 (2H, m, Ph), 7.41-7.45 (2H, m, Ph), 7.31-7.35 (1H, m, Ph), 7.16 (1H, br s, exchangeable with D2O, —NH), 7.01 (1H, s, H-4′), 3.35 (2H, br s, H-8), 2.98 (2H, br s, H-5), 1.93-1.95 (4H, m, H-6,7); 13C NMR (100 MHz, CDCl3): δ 162.3, 158.6, 153.7, 151.9, 145.3, 143.3, 137.0, 133.9, 129.5, 128.9, 128.4, 126.1, 124.3, 102.7, 100.1, 29.1, 28.4, 23.1, 22.5; LC-MS (positive ion mode): m/z 419, 421 (M+H)+.

Sources & evidence

ORD record
ord-50fa425d48144e3d86dd146465b8d6c4
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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