Water → HCID 17848320, compound

HRID 1352733Notes

Reaction equation

HRID 1352733 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=2)[C:5]([C:19]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[O:20])=[CH:4][N:3]=1.[C-]#N.[K+].OC1CC[NH:40][CH2:39]C1.O>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[C:39]([C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=2)[C:5]([C:19]([C:21]2[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=2)=[O:20])=[CH:4][N:3]=1)#[N:40]

Participants

7

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 79341Piperidin-4-olHCID 17848364HCID 17848364, compound

Product 1

HCID 17848320HCID 17848320, compound

Reagents, catalysts & solvents 2

HCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 101 mg of 2-chloro-5-(3,4,5-trimethoxyphenylcarbonyl)-4-(3-chloro-4-methoxybenzylamino)pyrimidine prepared in above Example 1-(3), potassium cyanide 27.5 mg and palladium chloride triphenylphosphine 3 mg in dimethylformamide 3 ml is stirred at 120° C. for 7 hours. To the reaction mixture is added 4-hydroxypiperidine, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is poured into water and is twice extracted with ethyl acetate. The extract is washed with water and brine in order, dried over anhydrous sodium sulfate and evaporated to dryness to give 2-cyano-5-(3,4,5-trimethoxyphenylcarbonyl)-4-(3-chloro-4-methoxybenzylamino)pyrimidine as a yellow solid, 7.5 mg. mp 140–143° C.

Workup

  1. extractionis twice extracted with ethyl acetate
  2. washThe extract is washed with water and brine in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0af15a45f8374c0eb56b850f12efa721
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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