Water → HCID 10401172, compound

HRID 860154Notes

Reaction equation

HRID 860154 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.O>CN(C)C=O>[CH3:15][C:12]1[N:13]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:14]=[C:10]([C:9]#[C:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 178418884HCID 178418884, compound

Product 1

HCID 10401172HCID 10401172, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine (II-1) (87 mg, 0.44 mmol) dissolved in 3 mL dimethyl formamide. Potassium carbonate (122 mg, 0.88 mmol) and 2-chloro-pyrimidine (76 mg, 0.66 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was poured into 60 mL water and extracted three times with ethyl acetate (50 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was treated with ethyl acetate (2 mL) and diisopropyl ether (2 mL). The solid was filtered off and washed with little diisoppropyl ether. The desired compound was as an off-white solid (49 mg, 50%), mp=164–165° C., MS: m/e=276.1 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. extractionextracted three times with ethyl acetate (50 mL each)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. additionThe crude product was treated with ethyl acetate (2 mL) and diisopropyl ether (2 mL)
  7. filtrationThe solid was filtered off
  8. washwashed with little diisoppropyl ether

Sources & evidence

ORD record
ord-d3b58e802e434fe4b07f7b7537c072d1
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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