Benzylamine → 8-Cyclopentyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 876647Notes

Reaction equation

HRID 876647 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([CH:13]=O)=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([CH2:19][C:20](O)=[O:21])#N.C(N)C1C=CC=CC=1>C(O)(=O)C>[CH:1]1([N:6]2[C:7]3[N:8]=[C:9]([S:15][CH3:16])[N:10]=[CH:11][C:12]=3[CH:13]=[CH:19][C:20]2=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 9740Cyanoacetic acidHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 108013948-Cyclopentyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (9), (1 g, 4.2 mmol), 1.2 equivalent of cyanoacetic acid, and a catalytic amount of benzylamine was taken into acetic acid and refluxed for about 6 h. After completion of the reaction by TLC, the reaction mixture was cooled to room temperature and product precipitated from the reaction mixture. Additional product was precipitated from the reaction mixture via the addition of hexane. The resultant solid was collected, washed with saturated NaHCO3, water, and subsequently dried under vacuum. The resultant crude product (10) was recrystallized in 2-propanol.

Workup

  1. temperaturerefluxed for about 6 h
  2. customAfter completion of the reaction by TLC
  3. customproduct precipitated from the reaction mixture
  4. customAdditional product was precipitated from the reaction mixture via the addition of hexane
  5. customThe resultant solid was collected
  6. washwashed with saturated NaHCO3, water
  7. customsubsequently dried under vacuum
  8. customThe resultant crude product (10) was recrystallized in 2-propanol

Sources & evidence

ORD record
ord-d2967fb68f0e448cb96a291cffe67200
Source dataset
uspto-grants-2015_03
Patent number
US08987267B2

Reaction notes

Loading…