Dimethylformamide → Pyrazin-2-yl-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamine

HRID 1529819Notes

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.N[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH2:17]1.[OH-].[Na+].C[N:25](C=O)C>>[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[NH:25][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

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 14798Sodium Hydroxide

HCID 54017740pyrazin-1(2H)-amine

HCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377309Pyrazin-2-yl-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamineYield 65%

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (600 mg, 2.20 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 4-aminopyrazine (310 mg, 3.30 mmol) and powdered NaOH (260 mg, 6.60 mmol) at rt. Work-up as described in example 2, gave the product as a pale yellow color solid (470 mg, 65%), mp 192-194° C. 1H NMR (400 MHz, CDCl3): δ 9.94 (1H, s), 8.56 (1H, s), 8.29 (1H, s), 8.23 (1H, s), 7.93 (1H, s, exchangeable with D2O), 3.14 (2H, s), 2.96 (2H, s), 2.01 (2H, s), 1.95 (2H, s); 13C NMR (100 MHz, CDCl3): δ 171.9, 153.4, 151.5, 149.1, 141.9, 138.8, 137.7, 126.7, 120.1, 28.2, 28.1, 22.7, 22.5; LC-MS (negative ion mode): m/z 328, 330 (M−H)−.

Sources & evidence

ORD record: ord-3faba1a37d164618916007ed12d03082
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090633B2

Reaction notes

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