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N-Methyl dicyclohexylamine → HCID 69922546, compound

HRID 2416545
Notes
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Reaction equation

HRID 2416545 reaction equation
O1CCOCC1.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1.CN(C1CCCCC1)C1CCCCC1.[C:34]([O:39][CH2:40][CH3:41])(=[O:38])/[CH:35]=[CH:36]/[CH3:37]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:40]([O:39][C:34](=[O:38])/[CH:35]=[C:36](/[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1)\[CH3:37])[CH3:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24210N-Methyl dicyclohexylamineHCID 312751,4-DioxaneHCID 429065Ethyl trans-crotonateHCID 222875442-(4-Bromophenyl)pyrimidine

Product 1

HCID 69922546HCID 69922546, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 2734635
Tri-tert-butylphosphine tetrafluoroborate
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 8857Ethyl AcetateSolvent

Procedure

Dioxane (2 mL) was added to a mixture of 2-(4-bromophenyl)pyrimidine (0.59 g, 2.51 mmol, prepared as described in U.S. Pat. No. 5,780,473), tri-t-butylphosphonium tetrafluoroborate (36 mg, 0.12 mmol), and tris(dibenzylideneacetone)dipalladium(0) (57 mg, 0.062 mmol). N-Methyldicyclohexylamine (0.64 mL, 2.99 mmol) and ethyl crotonate (0.62 mL, 4.99 mmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. Purification by chromatography (SiO2, 5:1 hexane/ethyl acetate) provided 0.47 g (70%) of the title compound as an off-white solid. MS 269 (M+H)+.

Workup

  1. customprepared
  2. filtrationfiltered through a small plug of silica gel which
  3. washwas washed with additional ethyl acetate
  4. concentrationthe combined filtrates were concentrated
  5. customPurification by chromatography (SiO2, 5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1d8cf2c969e04f8c849c3abb06db7d3e
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825170B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes