Diisopropylethylamine → HCID 50997147, compound

HRID 1399679Notes

Reaction equation

HRID 1399679 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.CC1(C)C(C)(C)OB([C:40]2[CH:48]=[C:47]3[C:43]([CH2:44][CH2:45][C:46]3=[O:49])=[CH:42][CH:41]=2)O1>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>[CH3:16][C:6]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([C:40]2[CH:48]=[C:47]3[C:43](=[CH:42][CH:41]=2)[CH2:44][CH2:45][C:46]3=[O:49])[N:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 177500786-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-oneHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 50997147HCID 50997147, compoundYield 56.5%

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) (0.059 mg; 0.05 mmol), N,N-diisopropylethylamine (0.345 mL; 2 mmol) and intermediate 18 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (0.325 g; 1.25 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 0.117 g (56%) 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-1a9c946d08a14cfd9db3f31fe390a24a
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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