6-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester → 6-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094511Notes

Reaction equation

HRID 1094511 reaction equation
[CH3:1][O:2][Na].[CH3:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH2:25]Br)[N:20]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7]>CO.CCOC(C)=O.O>[CH3:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][O:2][CH3:1])[N:20]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

6

Reactant 2

HCID 666399346-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl esterHCID 178418582HCID 178418582, compound

Product 1

HCID 591759856-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

760 μl (4.12 mMol) of a 5.4 M solution of MeONa in MeOH are added to a solution of 1.28 g (3.43 mMol) 6-(2-bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester in 70 ml MeOH. After 22 h stirring at rt, the mixture is diluted with EtOAc and water, the aq. layer separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 19: 1→1:3) gives the title compound: MS: [M+1]+=325; 1H NMR (CDCl3): δ ppm 9.06 (d, 1H), 8.66 (d, 1H), 8.24 (d, 1H), 8.03 (d, 1H), 7.70 (s, 1H), 7.59 (t, 1H), 7.46 (d, 1H), 6.82 (d, 1H), 4.58 (s, H2C), 4.06 (s, H3C), 3.53 (s, H3C).

Workup

  1. customthe aq. layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c82066a178e547c4bd6fd99f9f36edd5
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

Loading…