Diisopropylethylamine → Methyl 2-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399650Notes

Reaction equation

HRID 1399650 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[CH2:38][CH2:37][CH2:36][O:35][C:34]2[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][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>[O:32]1[CH2:38][CH2:37][CH2:36][O:35][C:34]2[CH:39]=[C:40]([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:41]=[CH:42][C:33]1=2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27763983,4-Dihydro-2H-1,5-benzodioxepin-7-ylboronic acidHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955841Methyl 2-(4-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoateYield 85.1%

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 (0.08 g; 0.25 mmol), tetrakis(triphenylphosphine) palladium(0) (0.029 mg; 0.025 mmol), N,N-diisopropylethylamine (0.173 mL; 1 mmol) and 3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylboronic acid (0.097 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 0.092 g (75%) 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-f9f4d363cad546ac81660ad9b285dfb4
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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