Imidazole → HCID 86632019, compound

HRID 419737Notes

Reaction equation

HRID 419737 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][C:13]([CH3:16])([OH:15])[CH3:14])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.N1C=CN=C1.C(OCC)C.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>C(Cl)Cl.O.CO>[Cl:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][C:13]([CH3:16])([O:15][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH3:14])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 86632017HCID 86632017, compound

Product 1

HCID 86632019HCID 86632019, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Charge 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yn-2-ol (3.35 g, 1.0 eq), imidazole (2.9 g, 3.0 eq), TEA (2.16 g, 1.5 eq) and diethyl ether (84 mL) at RT. Cool the reaction mass to 0° C. and add trimethyl silyl chloride (1.53 g, 1.0 eq). Stir the reaction mass at RT for 4 h. Monitor the reaction by TLC (5% MeOH in DCM). Charge chilled DM water and extract with diethyl ether. Wash the ether layer with saturated aq. sodium chloride. Dry the organic layer over anhydrous Na2SO4 and concentrate it under vacuum to get the desired compound (3.06 g, 70%).

Workup

  1. additionCharge
  2. extractionextract with diethyl ether
  3. washWash the ether layer with saturated aq. sodium chloride
  4. dry with materialDry the organic layer over anhydrous Na2SO4
  5. concentrationconcentrate it under vacuum

Sources & evidence

ORD record
ord-f9db649b681947039880319c79a71fce
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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