2-Methoxyethanol → 8-cyclopentyl-6-(2-methoxy-ethoxymethyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1272003Notes

Reaction equation

HRID 1272003 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(=O)([O-])[O-].[K+].[K+].[CH3:27][O:28][CH2:29][CH2:30][OH:31]>>[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:31][CH2:30][CH2:29][O:28][CH3:27])[C:14]2=[O:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 111873396-bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 112333818-cyclopentyl-6-(2-methoxy-ethoxymethyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Procedure

6-Bromomethyl-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.33 g, 3.75 mmol) was dissolved in 2-methoxyethanol (10 mL) to which potassium carbonate (0.778 g, 5.63 mmol) was added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then filtered and the salts washed with ethyl acetate. The combined organics were evaporated to give 8-cyclopentyl-6-(2-methoxy-ethoxymethyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a waxy solid (1.00 g, 76.3%). 1H NMR δ (400 MHz, CDCl3) 8.60 (s, 1H), 7.71 (t, J=1.6 Hz, 1H), 5.95 (m, 1H), 4.52 (d, J=1.6 Hz, 1H), 3.76 (m, 2H), 3.63 (m, 2H), 3.41 (s, 3H), 2.60 (s, 3H), 2.32 (m, 2H), 2.06 (m, 2H), 1.87 (m, 2H), 1.68 (m, 2H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered
  3. washthe salts washed with ethyl acetate
  4. customThe combined organics were evaporated

Sources & evidence

ORD record
ord-f503ca1330d04e70bf389aad335a853f
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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