Diisopropylethylamine → Methyl 2-(4-(3,4-dimethylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399632Notes

Reaction equation

HRID 1399632 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.[CH3:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[CH3:39]>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>[CH3:32][C:33]1[CH:34]=[C:35]([C:2]2[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]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)[CH:36]=[CH:37][C:38]=1[CH3:39]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27343483,4-Dimethylphenylboronic acidHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955309Methyl 2-(4-(3,4-dimethylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoateYield 71%

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 (0.159 g; 0.5 mmol) tetrakis(triphenylphosphine) palladium(0) (0.058 mg; 0.05 mmol), N,N-diisopropylethylamine (0.345 mL; 2 mmol) and 3,4-dimethylphenylboronic acid (0.225 g; 1.5 mmol) in DME-water (2 mL) for 1 h. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.138 g (71%) of the title compound.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane

Sources & evidence

ORD record
ord-26caba9bef5d4c09bd27f7e36da7cad7
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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