Potassium Carbonate → HCID 86634063, compound

HRID 1041637Notes

Reaction equation

HRID 1041637 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([N:6]([CH2:8][CH2:9][C:10]#[N:11])[CH3:7])=[O:5].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:10]([CH2:9][CH2:8][N:6]([CH3:7])[C:4](=[O:5])[C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[NH:1][C:19]1[C:20]([Cl:24])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)#[N:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 28386326HCID 28386326, compound

Product 1

HCID 86634063HCID 86634063, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-N-(2-cyano-ethyl)-N-methyl-benzamide (5.73 g, 28.2 mmol) in N,N-Dimethylformamide (50 mL) was treated with 2,4,5-Trichloro-pyrimidine (4.00 mL, 34.9 mmol) and Potassium carbonate (5.8 g, 42 mmol). The mixture was heated at 80° C. for 4 h, then cooled to room temperature and stirred for 4 days. The reaction was diluted with 200 mL water, extracted with DCM (200 mL, then 2×50 mL). The combined organics were washed 1×100 mL brine, dried over sodium sulfate and conc. in vacuo to give an oil, which was chromatographed (ISCO 330 g silica gel, 0-80% EtOAc:Hex). The product eluted with ˜60% EtOAc to afford N-(2-Cyano-ethyl)-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide as an oil (5.0 g, 50%). 1H-NMR (CDCl3): 9.36 (s, 1H), 8.34 (d, 1H, J=8.4 Hz), 8.22 (s, 1H), 7.53 (m, 1H), 7.38 (m, 1H), 7.21 (m, 1H), 3.81 (m, 2H), 3.22 (s, 3H), 2.80 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with DCM (200 mL
  3. washThe combined organics were washed 1×100 mL brine
  4. dry with materialdried over sodium sulfate and conc. in vacuo
  5. customto give an oil, which
  6. customwas chromatographed (ISCO 330 g silica gel, 0-80% EtOAc:Hex)
  7. washThe product eluted with ˜60% EtOAc

Sources & evidence

ORD record
ord-c81d3359fa1249129e4252b2f3b2fda9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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