Potassium Carbonate → 6-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazole

HRID 1846466Notes

Reaction equation

HRID 1846466 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([OH:14])[CH:11]=[C:12]([CH3:13])[C:6]=2[N:5]=1.[Cl:15][C:16]1[CH:21]=[C:20](Cl)[N:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:15][C:16]1[N:17]=[CH:18][N:19]=[C:20]([O:14][C:10]2[CH:11]=[C:12]([CH3:13])[C:6]3[N:5]=[C:4]([CH2:3][O:2][CH3:1])[NH:8][C:7]=3[CH:9]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 669782392-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-ol

Product 1

HCID 866639136-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

0.77 g (4.00 mmol) 2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-ol and 0.68 g (4.40 mmol) 4,6-dichloropyrimidine in 5.0 mL DMF were combined with 1.66 g (12.0 mmol) potassium carbonate and stirred for 8 h at 70° C. Then ice water was added and the substance was extracted with ethyl acetate and concentrated by rotary evaporation i.vac. The residue was purified by preparative HPLC-MS. The fractions containing product were combined and evaporated down i.vac.

Workup

  1. extractionthe substance was extracted with ethyl acetate
  2. concentrationconcentrated by rotary evaporation i.vac
  3. customThe residue was purified by preparative HPLC-MS
  4. additionThe fractions containing product
  5. customevaporated down i.vac

Sources & evidence

ORD record
ord-55f5ac9dc65742c381a3894364a0fbee
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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