Ethyl Bromide → 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine

HRID 841019Notes

Reaction equation

HRID 841019 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([N:12]2[CH2:18][CH2:17][C:16]3[CH:19]=[CH:20][S:21][C:15]=3[CH2:14][CH2:13]2)[N:3]=1.[CH2:22](Br)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]([O:8][C:6]1[N:7]=[C:2]([CH3:1])[N:3]=[C:4]([N:12]2[CH2:18][CH2:17][C:16]3[CH:19]=[CH:20][S:21][C:15]=3[CH2:14][CH2:13]2)[C:5]=1[N+:9]([O-:11])=[O:10])[CH3:23]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 1356711622-Methyl-5-nitro-6-(4,5,7,8-tetrahydro-thieno[2,3-d]azepin-6-yl)-3H-pyrimidin-4-one

Product 1

HCID 226207656-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 2 2-methyl-5-nitro-6-(4,5,7,8-tetrahydro-thieno[2,3-d]azepin-6-yl)-3H-pyrimidin-4-one (example 9) was treated with ethyl bromide in N,N-dimethylformamide in the presence of potassium carbonate at room temperature to yield 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine as light yellow amorphous solid; MS: [M+H]+=335; and 3-ethyl-2-methyl-5-nitro-6-(4,5,7,8-tetrahydro-thieno[2,3-d]azepin-6-yl)-3H-pyrimidin-4-one as yellow foam; MS: [M+H]+=335.

Sources & evidence

ORD record
ord-2d02d60cce5a4ed18b47f136573ddd84
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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