Isopropanol → 2-Chloro-6-(4-fluorophenyl)-4-[(propan-2-yl)oxy]pyrido[3,2-d]pyrimidine

HRID 1517455Notes

Reaction equation

HRID 1517455 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[C:6](Cl)[C:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1.[CH:22]([OH:25])([CH3:24])[CH3:23]>>[Cl:3][C:4]1[N:5]=[C:6]([O:25][CH:22]([CH3:24])[CH3:23])[C:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 596478432,4-Dichloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine

Product 1

HCID 576983452-Chloro-6-(4-fluorophenyl)-4-[(propan-2-yl)oxy]pyrido[3,2-d]pyrimidineYield 30%

Procedure

Sodium hydride (12 mg of a 60% of a dispersion in mineral oil, 0.3 mmol) was added to isopropanol (5 ml). The mixture was stirred at room temperature for 10 minutes. Then, 2,4-dichloro-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (60 mg, 0.2 mmol) was added to this solution. The resulting mixture was stirred at room temperature for another 40 minutes. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of isopropanol and dichloromethane in a volume ratio of 1:200, yielding the pure title compound (21 mg, yield 30%) as a white solid which was characterised as follows: MS (m/z): 318 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for another 40 minutes
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography
  4. additiona mixture of isopropanol and dichloromethane in a volume ratio of 1:200

Sources & evidence

ORD record
ord-1940552be3dc44f28588f5495f9a4198
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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