Pyridine → HCID 57460379, compound

HRID 1673829Notes

Reaction equation

HRID 1673829 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:20]2[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([CH3:16])=[N:11][C:10]=1[CH2:17][CH2:18][CH3:19].[CH3:28][C:29]1([CH3:42])[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34](B(O)O)[CH:35]=2)[O:30]1.N1C=CC=CC=1.C(N(CC)CC)C>C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:28][C:29]1([CH3:42])[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([N:13]3[C:14](=[O:15])[C:9]([CH2:8][C:7]4[CH:6]=[CH:5][C:4]([C:20]5[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=5)=[CH:3][C:2]=4[F:1])=[C:10]([CH2:17][CH2:18][CH3:19])[N:11]=[C:12]3[CH3:16])[CH:35]=2)[O:30]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 23005346B-(3,4-Dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)boronic acidHCID 1360269433'-Fluoro-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 57460379HCID 57460379, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3′-fluoro-4′-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.72 g), (2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)boronic acid (0.82 g), copper(II) acetate (0.73 g), pyridine (0.81 mL), triethylamine (1.4 mL), molecular sieves 4 A (1.5 g) and dichloromethane (10 mL) was stirred for 16 hr. The reaction mixture was diluted with ethyl acetate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.73 g, 70%) as a pale-yellow liquid.

Workup

  1. filtrationthe insoluble material was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c67e8422b527473c908d9c60b102bd19
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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