Water → HCID 68647844, compound

HRID 1163033Notes

Reaction equation

HRID 1163033 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.[CH:23]([CH:25]=[CH2:26])=O.C([N:29](CC)CC)C.O>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:23](/[CH:25]=[CH:26]/[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:4]([CH2:3][C:2]([CH3:22])([CH3:21])[CH3:1])[C:5]2[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=2)=[CH:15][CH:16]=1)#[N:29]

Participants

7

Reactant 4

HCID 962WaterHCID 7847AcroleinHCID 8471TriethylamineHCID 44450361HCID 44450361, compound

Product 1

HCID 68647844HCID 68647844, compoundYield 638.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-[(2,2-Dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile (0.1 g, 0.2 mmoles), acrolein (0.02 ml, 0.3 mmoles), and triethylamine (0.04 ml, 0.3 mmoles) are dissolved in 5 ml of acetonitrile and Pd(OAc)2 (2.6 mg, 0.012 mmoles) is added at rt. The mixture is stirred at 100° C. for overnight. 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 423 mg of desired 4-[[4-((E)-2-cyano-vinyl)-benzyl]-(2,2-dimethyl-propyl)-amino]-pyrimidine-2-carbonitrile in 45% 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-224fc9820ea441e89c0c55488d899ded
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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