Formamide → 5,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one

HRID 2189017Notes

Reaction equation

HRID 2189017 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([O:13]CC)=O.C([O-])(=O)C.[NH4+].[CH:21]([NH2:23])=O>O>[N:1]1[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]=2[C:11](=[O:13])[NH:23][CH:21]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylateHCID 517165Ammonium Acetate

Product 1

HCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.7 g, 3.1 mmole), ammonium acetate (0.31 g, 4.04 mmole) and formamide (0.67 ml, 16.8 mmole), was stirred under reflux at 140° C. for 13 hours. It was then cooled, diluted with water (20 ml), extracted with ethyl acetate (3×35 ml), dried, concentrated and purified by column chromatography to obtain the pure 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A09) (0.53 gm, 82%).

Workup

  1. temperatureIt was then cooled
  2. extractionextracted with ethyl acetate (3×35 ml)
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-ea34f81d4bbd4c18bccf29efdb55b453
Source dataset
uspto-grants-2012_12
Patent number
US08324227B2

Reaction notes

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