Morpholine → 6-(4-Fluorophenyl)-4-(morpholin-4-yl)pyrido[3,2-d]pyrimidine

HRID 1517440Notes

Reaction equation

HRID 1517440 reaction equation
Cl[C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O1CCOCC1>[O:22]1[CH2:23][CH2:24][N:19]([C:2]2[C:3]3[N:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 579067564-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine

Product 1

HCID 576983666-(4-Fluorophenyl)-4-(morpholin-4-yl)pyrido[3,2-d]pyrimidineYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (56 mg, 0.2 mmol) and morpholine (200 μl) in dioxane (5 ml) was refluxed for 1 hour. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 1:60, yielding the title compound (60 mg, yield 97%) as a white solid which was characterised by its mass spectrum as follows: MS (m/z): 311 ([M+H]+, 100).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography
  4. additiona mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-7ba9724f6bac4fb6b3406d52817582c5
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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