4-Iodo-2-(methylthio)pyrimidine → 5-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridine

HRID 396370Notes

Reaction equation

HRID 396370 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:10][C:5]2=[CH:4][CH:3]=1.[CH3:18][S:19][C:20]1[N:25]=[C:24](I)[CH:23]=[CH:22][N:21]=1>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]([C:22]3[CH:23]=[CH:24][N:25]=[C:20]([S:19][CH3:18])[N:21]=3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 224861255Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridine

Product 1

HCID 224861505-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridineYield 71.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

KN(TMS)2 (1.42 g 7.16 mmol) in toluene (7 ml) is added at 0° C. to a solution of 5Chloro-2-(4fluorophenyl)imidazo[4,5-b]pyridine (1.9 g 6.66 mmol) in DMF (25 ml). After stirring 1 h at room temperature, 2-methylthio-4-iodopyrimidine (1.8 g 7.1 mmol) in toluene (7 ml) is added dropwise and heated for 20 h at 120° C. The reaction mixture is poured on water and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the crystalline crude product, which after recrystallisation from ethyl acetate yields the title compound as colorless crystals (1.76 g 67%).

Workup

  1. temperatureheated for 20 h at 120° C
  2. additionThe reaction mixture is poured on water
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield the crystalline crude product, which
  8. customafter recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e93dd8a27bfa49c7be7a80a38dea4065
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Reaction notes

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