Methanol → HCID 57829738, compound

HRID 1855493Notes

Reaction equation

HRID 1855493 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10](Cl)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[C:18](=[O:21])([O-])[O-].[K+].[K+].C1(C2C=CC=CC=2)C=CC=CC=1.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]2[CH:47]=[C:46](CO)[N:45]=[CH:44]2)=[CH:39][CH:38]=1>O1CCOCC1.CN(C)C(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH:36][C:37]2[CH:38]=[CH:39][C:40]([N:43]3[CH:47]=[CH:46][N:45]=[C:44]3[CH2:18][OH:21])=[CH:41][CH:42]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 887MethanolHCID 7095BiphenylHCID 11430Potassium CarbonateHCID 13399964HCID 13399964, compoundHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 57829738HCID 57829738, compoundYield 131.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-benzyl-2-chloro-6-methyl-pyrimidine (104 mg, 0.48 mmol), 1-(4-amino-phenyl)-1H-imidazol-2-yl]-methanol (90 mg, 0.48 mmol) and potassium carbonate (1.33 g, 9.5 mmol) in dioxane (4 mL) and N,N-dimethylacetamide (1 mL) was degassed with nitrogen. Palladium(II) acetate (4.3 mg, 0.019 mmol) and 2-dicyclohexylphosphino)bi-phenyl (13.6 mg, 0.038 mmol) were added and the reaction mixture was irradiated in a microwave oven at 200° C. for 30 minutes. [1-(4-Amino-phenyl)-1H-imidazol-4-yl]-methanol (43 mg, 0.19 mmol) was added and the reaction mixture was irradiated in a microwave oven at 200° C. for another 25 minutes. The reaction mixture was filtered; the filtrate was diluted with ethyl acetate, washed with water and brine, dried with magnesium sulfate and concentrated in vacuo. Purification by column chromatography on silica eluting with dichloromethane/methanol (14:1 v/v) afforded the title compound as a light yellow solid (93 mg, 52%). MS ISP (m/e): 372.2 [(M+H)+]. Mp 95-98° C.

Workup

  1. customwas degassed with nitrogen
  2. customthe reaction mixture was irradiated in a microwave oven at 200° C. for 30 minutes
  3. customthe reaction mixture was irradiated in a microwave oven at 200° C. for another 25 minutes
  4. filtrationThe reaction mixture was filtered
  5. additionthe filtrate was diluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography on silica eluting with dichloromethane/methanol (14:1 v/v)

Sources & evidence

ORD record
ord-e4efc3a95f2d4029a7e45f3752f7a8d8
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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