Sodium Hydroxide → (2,6-Dichloropyrimidin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamine

HRID 1529818Notes

Reaction equation

HRID 1529818 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[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([Cl:23])[N:17]=1.[OH-].[Na+]>CN(C=O)C>[Cl:23][C:18]1[N: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)[CH:21]=[C:20]([Cl:22])[N:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 823874-Pyrimidinamine, 2,6-dichloro-HCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377308(2,6-Dichloropyrimidin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamineYield 68.5%

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 (10 mL) was added sequentially 4-amino-2,6-dichloropyrimidine (450 mg, 2.75 mmol) and powdered NaOH (220 mg, 5.50 mmol) at rt. Work-up of the mixture as described in example 2, gave the product as an off-white color solid (500 mg, 68%), mp 268-270° C. 1H NMR (400 MHz, CDCl3): δ 8.67 (1H, s), 8.64 (1H, s), 8.23 (1H, s, exchangeable with D2O), 3.11 (2H, t, J=6.1 Hz), 2.97 (2H, t, J=6.1 Hz), 2.01-2.06 (2H, m), 1.92-1.98 (2H, m); 13C NMR (100 MHz, CDCl3): δ 172.9, 162.7, 160.0, 159.2, 152.4, 151.0, 142.7, 126.3, 121.3, 107.8, 28.3, 28.2, 22.7, 22.4; LC-MS (negative ion mode): m/z 396, 398, 400, 402 (M−H)−.

Sources & evidence

ORD record
ord-af8740bd72154c2a82b1dfcdda726faa
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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