Water → 6-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094508Notes

Reaction equation

HRID 1094508 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([CH3:24])[N:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:21]3[CH:22]=[C:17]([Cl:16])[N:18]=[C:19]([CH3:24])[N:20]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 11367671Methyl 6-hydroxy-1-naphthoate

Product 1

HCID 866651676-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of 6.0 g (29.7 mMol) 6-hydroxy-naphthalene-1-carboxylic acid methyl ester (see Step 3.1), 7.6 g (46.6 mMol) 4,6-dichloro-2-methylpyrimidine and 13.9 g (65 mMol) K3PO4 in 50 ml NMP is stirred for 4 days at rt. The mixture is poured into ½ l water and the title compound filtered off, washed with water and dried (HV, 80° C.): HPLC: tRet=17.2.

Workup

  1. filtrationthe title compound filtered off
  2. washwashed with water
  3. customdried (HV, 80° C.)

Sources & evidence

ORD record
ord-4cec7875173242659067ec882b164533
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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