Formamide → 1,5,6,7-Tetrahydro-4H-cyclopenta(4,5)thieno(2,3-d)pyrimidin-4-one

HRID 22785Notes

Reaction equation

HRID 22785 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([O:12]CC)=O.O.[CH:16]([NH2:18])=O>>[N:1]1[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][C:4]=3[C:3]=2[C:10](=[O:12])[NH:18][CH:16]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 264105ethyl 2-amino-4H,5H,6H-cyclopenta[b]thiophene-3-carboxylate

Product 1

HCID 2034201,5,6,7-Tetrahydro-4H-cyclopenta(4,5)thieno(2,3-d)pyrimidin-4-one

Procedure

A suspension of 11.37 g ethyl 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate in 40 mL formamide was heated for 4 h to 190° C. using a heating mantle, then cooled and poured into 400 mL water. The mixture was then filtered to remove the solid product. The solids were washed successively with 30 mL EtOAc and 200 mL diethyl ether, air dried overnight, then vacuum oven dried for 3 h. The material was used in the subsequent reactions without further purification.

Workup

  1. temperaturewas heated for 4 h to 190° C.
  2. temperaturecooled
  3. filtrationThe mixture was then filtered
  4. customto remove the solid product
  5. washThe solids were washed successively with 30 mL EtOAc and 200 mL diethyl ether, air
  6. customdried overnight
  7. customvacuum oven dried for 3 h
  8. customThe material was used in the subsequent reactions without further purification

Sources & evidence

ORD record
ord-7015bc9ba75548c697063adb8e79b4d9
Source dataset
uspto-grants-2005_02
Patent number
US06849638B2

Reaction notes

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