Diisopropylethylamine → Methyl 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399687Notes

Reaction equation

HRID 1399687 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.C[O:33][C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1B(O)O>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:33][C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 18414543(2-Methoxy-4-methylphenyl)boronic acidHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 136126955Methyl 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoateYield 65%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

This compound was prepared according to general method E from methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.10 g; 0.314 mmol), tetrakis(triphenylphosphine) palladium(0) (0.036 mg; 0.031 mmol), N,N-diisopropylethylamine (0.216 mL; 1.25 mmol) and 2-methoxy-4-methylphenylboronic acid (0.078 g; 0.47 mmol in DME-water (1 mL) for 20 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 0.082 g (65%) of the title compound as a colorless oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane

Sources & evidence

ORD record
ord-be28616ad4ab4fd387d64f5bdd9836d4
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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