Methyl Isobutyl Ketone → 7-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

HRID 2210808Notes

Reaction equation

HRID 2210808 reaction equation
ClCC[C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][S:13][C:7]2=[N:6][C:5]=1[CH3:14].C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[CH3:14][C:5]1[N:6]=[C:7]2[S:13][CH:12]=[CH:11][N:8]2[C:9](=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 8178726-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

Product 1

HCID 5970657-Methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.75 g of 6-(2-chloroethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, 3.1 g of the base of compound (1), 1.6 g of sodium carbonate and 100 ml of 4-methyl-2-pentanone was stirred for 72 hours at reflux temperature. After cooling, water was added and the whole was stirred. The separated aqueous layer was extracted with dichloromethane. The combined organic layers were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5→CH2Cl2 /CH3OH(NH3) 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile. The precipitate was filtered off and dried, yielding 1.70 g (32.7%) of 6-[2-[4-(5,6-dihydro-7-methyl-10(7H)-imidazo[1,2-a]-pyrrolo]3,2-d]azepin-10-ylidene)-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]-pyrimidin-5-one; mp. 201.4° C. (comp. 5).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringthe whole was stirred
  4. extractionThe separated aqueous layer was extracted with dichloromethane
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5→CH2Cl2 /CH3OH(NH3) 95:5)
  9. customThe eluent of the desired fraction was evaporated
  10. customthe residue was crystallized from acetonitrile
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-a8eb8efef80e4a48b115e56dfaebf13b
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

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