Methanol → 5-Amino-8-cyclopropyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2386676Notes

Reaction equation

HRID 2386676 reaction equation
[N:1]([C:4]1[C:13]2[CH:12]=[N:11][C:10]([S:14][CH3:15])=[N:9][C:8]=2[N:7]([CH:16]2[CH2:18][CH2:17]2)[C:6](=[O:19])[CH:5]=1)=[N+]=[N-].C(Cl)Cl.CO>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[C:13]2[CH:12]=[N:11][C:10]([S:14][CH3:15])=[N:9][C:8]=2[N:7]([CH:16]2[CH2:18][CH2:17]2)[C:6](=[O:19])[CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 57929482HCID 57929482, compound

Product 1

HCID 579294555-Amino-8-cyclopropyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 125.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium hydroxide on carbon (10% wt., 150 mg) was added to a solution of 5-azido-8-cyclopropyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.5 g) in glacial acetic acid (80 mL) and the resulting mixture was stirred under H2 (balloon pressure) for 2 h. A mixture of DCM and MeOH (80/20, 100 mL) was added and the resulting mixture was filtered over a CELITE™ pad and the filter cake was washed with a mixture of DCM and MeOH (80/20, 500 mL). The filtrate was concentrated under reduced pressure to give 1.7 g 5-amino-8-cyclopropyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a green solid without further purifications. MS=248.9 [M+H]+.

Workup

  1. additionwas added
  2. filtrationthe resulting mixture was filtered over a CELITE™ pad
  3. washthe filter cake was washed with a mixture of DCM and MeOH (80/20, 500 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9d68a57545649688edaace3a351311a
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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