Potassium Phosphate, Tribasic → 6-(6-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094518Notes

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[C:17]1[CH:22]=[C:21]([CH2:23][O:24][CH3:25])[N:20]=[CH:19][N:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:17]3[CH:22]=[C:21]([CH2:23][O:24][CH3:25])[N:20]=[CH:19][N:18]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 3.4 g (16.8 mMol) 6-hydroxy-naphthalene-1-carboxylic acid methyl ester (see Step 3.1), 3.2 g (20.2 mMol) 4-chloro-6-(methoxymethyl)pyrimidine (preparation see: BE 64 1253, p. 38; or WO 2002/45652, p. 102) and 7.85 g (37 mMol) K3PO4 in 85 ml NMP is stirred for 4 h at 90° C. The cooled mixture is diluted with 0.4 l EtOAc and 0.4 l water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Chromatography (SiO2; CH2Cl2/EtOAc 19:1→9:1→4:1) gives the title compound: m.p.: 87-88° C.; MS: [M+1]+=325; TLC (CH2Cl2/EtOAc 4:1): Rf=0.28.

Workup

customthe aq. phase separated off
extractionextracted twice with EtOAc
washThe organic layers are washed twice with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-c967fd6d7a5e4de687f5d674f2aaffc2
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133886B2

Reaction notes

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