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

HRID 1399636Notes

Reaction equation

HRID 1399636 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.[O:32]1[C:36]2[CH:37]=[CH:38][C:39](B(O)O)=[CH:40][C:35]=2[CH2:34][CH2:33]1>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>[O:32]1[C:36]2[CH:37]=[CH:38][C:39]([C:2]3[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]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:3]=3)=[CH:40][C:35]=2[CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955799Methyl 2-(4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoateYield 91.4%

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 2,3-dihydrobenzofuran-5-ylboronic acid (0.246 g; 1.5 mmol) in DME-water (2 mL) for 30 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.184 g (91%) 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-06e4cdb137a4407ba559b6b635fd0f5c
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

Loading…