Sodium Methoxide → 6-(4-Fluorophenyl)-4-methoxypyrido[3,2-d]pyrimidin-2-amine

HRID 1517462Notes

Reaction equation

HRID 1517462 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:6]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:16]=[CH:15][C:7]=2[N:8]=[C:9]([NH:11]C(=O)C)[N:10]=1>C1COCC1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:16]=[CH:15][C:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:5]([O:2][CH3:1])[C:6]=3[N:18]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57698346N-(4-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-yl)acetamide

Product 1

HCID 576983386-(4-Fluorophenyl)-4-methoxypyrido[3,2-d]pyrimidin-2-amineYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (0.32 mL, 0.158 mmol; 0.5 N in MeOH) was added to a solution of N-[4-chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-2-yl]-acetamide (20 mg, 0.063 mmol) in THF (1.5 mL). After stirring at room temperature for 20 minutes, solvents were concentrated in vacuo and the residue was purified by RP HPLC using a C18 column with a gradient of H2O and 0.1% TFA-acetonitrile, to provide the pure title compound as a white solid (14 mg, yield 50%) which was characterised as follows: MS (m/z) 271.0 [M+H]+.

Workup

  1. concentrationsolvents were concentrated in vacuo
  2. customthe residue was purified by RP HPLC

Sources & evidence

ORD record
ord-5e6d90416e8a46138dd251a5b653c485
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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