Phosphorus oxychloride → 8-Chloro-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidine

HRID 1480812Notes

Reaction equation

HRID 1480812 reaction equation
[CH3:1][C:2]1[NH:13][C:12](=O)[C:5]2[N:6]=[C:7]([S:10][CH3:11])[N:8]=[CH:9][C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:12]1[C:5]2[N:6]=[C:7]([S:10][CH3:11])[N:8]=[CH:9][C:4]=2[CH:3]=[C:2]([CH3:1])[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 899960166-Methyl-2-(methylthio)pyrido[3,4-d]pyrimidin-8(7H)-one

Product 1

HCID 899960218-Chloro-6-methyl-2-(methylthio)pyrido[3,4-d]pyrimidineYield 52%

Procedure

A solution of 6-methyl-2-(methythio)pyrido[3,4-d]pyrimidin-8(7H)-one (Preparation 51, 100 mg, 0.483 mmol) in POCl3 (5 mL) was heated to 70° C. for 1 hour. The reaction mixture was concentrated in vacuo. The residue was partitioned between EtOAc (30 mL) and washed with water (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-20% EtOAc in cyclohexane to give the title compound (28.4 mg, 52%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between EtOAc (30 mL)
  3. washwashed with water (30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0-20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-75ddcff732b84c02a75104df913d278c
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

Loading…