Diisopropylethylamine → 2-Methyl-5-nitro-6-(4,5,7,8-tetrahydro-thieno[2,3-d]azepin-6-yl)-3H-pyrimidin-4-one

HRID 841018Notes

Reaction equation

HRID 841018 reaction equation
Br[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[S:13]1[C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:16]=2[CH:15]=[CH:14]1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:8][C:6]1[NH:5][C:4](=[O:9])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([N:20]2[CH2:21][CH2:22][C:16]3[CH:15]=[CH:14][S:13][C:17]=3[CH2:18][CH2:19]2)[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 115137774H,5H,6H,7H,8H-thieno[2,3-d]azepineHCID 1356171936-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one

Product 1

HCID 1356711622-Methyl-5-nitro-6-(4,5,7,8-tetrahydro-thieno[2,3-d]azepin-6-yl)-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the method described in example 1c 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one (example 1a) was treated with 5,6,7,8-tetrahydro-4H-thieno-[2,3-d]azepine [J. Heterocycl. Chem. (1985), 22(4), 1011-16] in N,N-dimethylformamide in the presence of N-ethyl-di-isopropylamine at room temperature to yield the title compound as yellow solid; m.p.>200° C.; MS: [M−H]−=305.

Sources & evidence

ORD record
ord-7116dad7195843bdba0712cdd1e555ff
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

Loading…