Acetic Acid → Acetic acid 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester

HRID 586471Notes

Reaction equation

HRID 586471 reaction equation
Br[CH2:2][C:3]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:6]2[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=2[CH:4]=1.[C:21]([OH:24])(=[O:23])[CH3:22]>C([O-])(=O)C.[Ag+]>[CH:16]1([N:13]2[C:6]3[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=3[CH:4]=[C:3]([CH2:2][O:24][C:21](=[O:23])[CH3:22])[C:14]2=[O:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 111873396-bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 11348177Acetic acid 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

Conditions

Temperature
110 °C

Procedure

6-Bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.33 g, 3.75 mmol), prepared as in Example 25, and silver acetate (1.03 g, 6.2 mmol) were added to glacial acetic acid (10 ml) and heated to 110° C. for 5 hours. The solvents then were evaporated at reduced pressure and the resulting residue was suspended in ethyl acetate and filtered. The solid obtained was recrystallized from ethyl acetate to provide acetic acid 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester as a solid (0.89 g, 71%). MS (APCI) M++1; Calc'd 334.11. Found 334.2.

Workup

  1. customThe solvents then were evaporated at reduced pressure
  2. filtrationfiltered
  3. customThe solid obtained
  4. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d7342037f30a4940a1b2d892f2bd268e
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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