Methanol → 2-Methanesulfinyl-pyrido[2,3-d]pyrimidin-7-ylamine

HRID 1826582Notes

Reaction equation

HRID 1826582 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9][C:7]=2[N:8]=1.C[OH:15]>ClCCl>[CH3:1][S:2]([C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9][C:7]=2[N:8]=1)=[O:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 221347182-(Methylthio)pyrido[2,3-d]pyrimidin-7-amine

Product 1

HCID 221347172-Methanesulfinyl-pyrido[2,3-d]pyrimidin-7-ylamineYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 10.63 g (55.3 mmol) of 2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-ylamine (Example 7) in 300 mL of dichloromethane and 300 mL of methanol is treated with 18.06 g (69.1 mmol) of (±)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine and stirred overnight. The suspension is filtered to remove a small amount of solid, concentrated to approximately 25 mL, and diluted with ethyl acetate. The solid is collected by filtration to give 9.27 g (80.5%) of the product, mp 180° C. (dec).

Workup

  1. filtrationThe suspension is filtered
  2. customto remove a small amount of solid
  3. concentrationconcentrated to approximately 25 mL
  4. additiondiluted with ethyl acetate
  5. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-eccdd4147e344f779af3bbb8fb7a497a
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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