Iodoethane → 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine

HRID 841013Notes

Reaction equation

HRID 841013 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[S:19][C:20]([CH3:22])=[N:21][C:15]=3[CH2:14][CH2:13]2)[N:3]=1.[CH2:23](I)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:23]([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[S:19][C:20]([CH3:22])=[N:21][C:15]=3[CH2:14][CH2:13]2)[C:5]=1[N+:9]([O-:11])=[O:10])[CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1356711572-methyl-6-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-5-nitro-3H-pyrimidin-4-one

Product 1

HCID 226207486-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.120 g (0.373 mmol) of 2-methyl-6-(2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-5-nitro-3H-pyrimidin-4-one (example 1), of 0.070 g (0.45 mmol) of the ethyl iodide and of 0.077 g (0.56 mmol) of potassium carbonate in 1.0 ml of N,N-dimethylformamide was stirred at room temperature for 4 hours. The reaction mixture was then poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was then chromatographed on silica gel using a 95:5 v/v mixture of dichloromethane and methanol as eluent giving in a first fraction 0.025 g (0.072 mmol, yield 19%) of the 6-(6-ethoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine as yellow amorphous solid; MS: [M+H]+=350.

Workup

  1. extractionextracted 3 times with 50 ml of ethylacetate
  2. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas then chromatographed on silica gel using
  6. additiona 95:5 v/v mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-8a28d3313f4944d4a09e17a37634294c
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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