Dimethylformamide → HCID 57839109, compound

HRID 733159Notes

Reaction equation

HRID 733159 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[C:5]([CH3:11])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1.C(OCC)(=O)C.[CH3:28][N:29](C)C=O>[C-]#N.[Zn+2].[C-]#N.[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>[CH3:11][C:5]1[C:6]([CH2:8][CH2:9][CH3:10])=[N:7][C:2]([C:28]#[N:29])=[N:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 57839132HCID 57839132, compound

Product 1

HCID 57839109HCID 57839109, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

To a solution of 2-chloro-5-methyl-4-propyl-6-(3-trifluoromethylphenyl)-pyrimidine (50 mg) in dimethylformamide (1 mL), was added zinc(II) cyanide (16 mg) and tetrakis(triphenylphosphine)-palladium(0) (16 mg). The suspension was heated in the microwave at 150° C. for 5 min, then poured into ethyl acetate (50 mL) and washed with water (2×10 mL). The organic layer was separated, dried over sodium sulphate and evaporated at reduced pressure. Preparative-HPLC afforded 5-methyl-4-propyl-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile as a yellow gum (11 mg). 1H NMR (CDCl3): δ 7.63-7.81 (m, 4H), 2.87 (t, 2H), 2.39 (s, 3H), 1.80-1.90 (m, 2H), 1.07 (t, 3H). MS m/z 306.4 (M+1), 100%.

Workup

  1. washwashed with water (2×10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-c232a715b48f475e8429c016821f21bf
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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