Sodium Methoxide → 5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine

HRID 1162213Notes

Reaction equation

HRID 1162213 reaction equation
F[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:12][C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[N:17]=[CH:16]3)=[N:5][CH:6]=[N:7]2.[CH3:29][O-:30].[Na+]>CO>[CH3:29][O:30][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:12][C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[N:17]=[CH:16]3)=[N:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 686183205-fluoro-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine

Product 1

HCID 686187925-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-fluoro-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine (10.2 g, 27.5 mmol) and sodium methoxide (4.46 g, 82.6 mmol) in methanol (250 ml) was heated at reflux for 24 hours. After cooling and evaporation of the solvents, the residue was dissolved in DCM. This solution was washed with water and brine and dried over MgSO4. Evaporation of the solvents gave 5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine as a beige solid (10.5 g, 100%); NMR spectrum (CDCl3) 4.11 (s, 3H), 5.75 (s, 2H), 6.87 (d, 1H), 6.91 (d, 1H), 7.19 (m, 1H), 7.57-7.42 (m, 4H), 7.64 (t, 1H), 8.09 (s, 1H), 8.22 (m, 1H), 8.59 (m, 2H), 9.83 (br s, 1H); Mass spectrum MH+ 383.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. customevaporation of the solvents
  5. dissolutionthe residue was dissolved in DCM
  6. washThis solution was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvents

Sources & evidence

ORD record
ord-cd4edf2cd9784f26aaa575a2105351fa
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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