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Diisopropylethylamine → Methyl 2-(4-(benzo[b]thiophen-5-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399654
Notes
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Reaction equation

HRID 1399654 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.[S:32]1[CH:36]=[CH:35][C:34]2[CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:39]=[CH:40][C:33]1=2>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>[S:32]1[CH:36]=[CH:35][C:34]2[CH:37]=[C:38]([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:39]=[CH:40][C:33]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27954552-(1-Benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955566Methyl 2-(4-(benzo[b]thiophen-5-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoateYield 45.1%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 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 (0.08 g; 0.25 mmol), tetrakis(triphenylphosphine) palladium(0) (0.029 mg; 0.025 mmol), N,N-diisopropylethylamine (0.173 mL; 1 mmol) and 2-(benzo[b]thiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.131 g; 0.5 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 0.047 g (42%) 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-fabf5d57ebfa4b1e91ffc8c6c2011704
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906906B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes