Formamide → HCID 68514832, compound

HRID 2189016Notes

Reaction equation

HRID 2189016 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:5][C:6]=1[C:7](OCC)=[O:8].C([O-])(=O)C.[NH4+].[CH:24]([NH2:26])=O>O>[C:16]([O:15][CH2:14][CH2:13][CH2:12][C:4]1[S:3][C:2]2[N:1]=[CH:24][NH:26][C:7](=[O:8])[C:6]=2[CH:5]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 713FormamideHCID 517165Ammonium AcetateHCID 68512929HCID 68512929, compound

Product 1

HCID 68514832HCID 68514832, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of ethyl 2-amino-5-(3-acetyloxypropyl)-thiophene-3-carboxylate (2.6 g, 9.7 mmole), ammonium acetate (0.74 g, 9.7 mmole) and formamide (8.64 ml, 19.2 mmole), was stirred under reflux at 145° C. for 12 hours. It was then cooled, diluted with water (20 ml), extracted with ethyl acetate (3×25 ml), dried, concentrated and purified by column chromatography to obtain the pure 6-(3-Acetoxypropyl)-thieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A26) (1.8 gm, 75%).

Workup

  1. temperatureIt was then cooled
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-b35faf497bae4b0d966576be09bbb8ef
Source dataset
uspto-grants-2012_12
Patent number
US08324227B2

Reaction notes

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