Iodoethane → 6-(2-Amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-3-ethyl-2-methyl-5-nitro-3H-pyrimidin-4-one

HRID 841015Notes

Reaction equation

HRID 841015 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][N:8]([C:11]3[N:16]=[C:15]([CH3:17])[NH:14][C:13](=[O:18])[C:12]=3[N+:19]([O-:21])=[O:20])[CH2:7][CH2:6][C:5]=2[N:22]=1.[CH2:23](I)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][N:8]([C:11]3[N:16]=[C:15]([CH3:17])[N:14]([CH2:23][CH3:24])[C:13](=[O:18])[C:12]=3[N+:19]([O-:21])=[O:20])[CH2:7][CH2:6][C:5]=2[N:22]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1356711606-(2-Amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-methyl-5-nitro-3H-pyrimidin-4-one

Product 1

HCID 226207556-(2-Amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-3-ethyl-2-methyl-5-nitro-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 2 the 6-(2-amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-2-methyl-5-nitro-3H-pyrimidin-4-one (example 3) was treated with the ethyl iodide in N,N-dimethylformamide in the presence of potassium carbonate at room temperature to yield the title compound as yellow solid; m.p.>200° C.; MS: [M+H]+=351.

Sources & evidence

ORD record
ord-a1da5822bc024ce29848d118c4c44f66
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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