Ethanol → 2-Isopropyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one

HRID 910184Notes

Reaction equation

HRID 910184 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=[O:5])C.Cl.[CH:19]([CH2:22][C:23]([NH2:25])=N)(C)C.[CH2:26](O)C>>[CH:22]([C:23]1[NH:25][C:4](=[O:5])[C:6]2[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][S:8][C:7]=2[N:17]=1)([CH3:19])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 189679323-Methylbutanimidamide hydrochloride

Product 1

HCID 288680672-Isopropyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one

Procedure

A stirred mixture of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (350.43 g, 1.54 mol), isopropylacetamidine hydrochloride (958.75 g, 7.7 mol) and ethanol (1500 ml) was heated under reflux for 18 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with a little cold ethanol, then crystallised from ethanol to give 2-Isopropyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one as a yellow solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with a little cold ethanol
  5. customcrystallised from ethanol

Sources & evidence

ORD record
ord-f133ed69a02a4fd199475b57d66357f8
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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