Water → HCID 57714110, compound

HRID 1163025Notes

Reaction equation

HRID 1163025 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1.[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:28]2[N:24]([CH3:23])[CH:25]=[N:26][CH:27]=2)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13901-MethylimidazoleHCID 11776TriphenylphosphineHCID 44450361HCID 44450361, compound

Product 1

HCID 57714110HCID 57714110, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-{(2,2-Dimethyl-propyl)-[4-iodo-benzyl]-amino}-pyrimidine-2-carbonitrile (200 mg, 0.5 mmoles), 1-methyl imidazole (0.2 ml, 2.5 mmoles), triphenylphosphine (26 mg, 0.10 mmoles) and CsCO3 (160 mg, 0.5 mmoles) are dissolved in 3 ml of DMF and Pd(OAc)2 (10 mg, 0.05 mmoles) is added at rt. The mixture is stirred at 120° C. for 18 h. Water is added and the organic layer is extracted with AcOEt washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 104 mg of desired 4-{(2,2-dimethyl-propyl)-[4-(3-methyl-3H-imidazol-4-yl)-benzyl]-amino}-pyrimidine-2-carbonitrile in 59% yield.

Workup

  1. extractionthe organic layer is extracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55e509367eda44c788517ad5e5352912
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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