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

HRID 586472Notes

Reaction equation

HRID 586472 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C:7]2=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:31])C=CC=CC=1.C(OCC)C>ClCCl>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16]([CH3:17])=[O:31])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C:7]2=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 11348177Acetic acid 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester

Product 1

HCID 11439492Acetic acid 8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic acid 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester (0.85 g, 2.55 mmol), prepared as in Example 26, and 2-benzenesulfonyl-3-phenyl-oxaziridine (0.8 g, 3.06 mmol) were mixed in dichloromethane (20 ml) and stirred at room temperature for 5 hours. To this mixture was added diethyl ether giving a solid precipitate which was filtered and dried in vacuo to provide acetic acid 8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl ester as a solid (0.81 g, (91%). MS (APCI) M++1; Calc'd 350.41. Found 350.2.

Workup

  1. filtrationwas filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-48cf82839edb4e2daefc13704c967ce4
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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