Potassium Carbonate → HCID 178428834, compound

HRID 1846505Notes

Reaction equation

HRID 1846505 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][C:9]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:10][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:18][C:19]1[N:20]=[CH:21][N:22]=[C:23]([O:17][C:4]2[CH:3]=[C:2]([CH3:1])[C:7]3[NH:8][C:9]([CH:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[N:10][C:6]=3[CH:5]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 178428965HCID 178428965, compound

Product 1

HCID 178428834HCID 178428834, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.35 g (0.84 mmol) 7-methyl-2-(tetrahydro-2H-pyran-4-yl)-1H-benzo[d]imidazol-5-ol and 0.14 mg (0.90 mmol) 4,6-dichloropyrimidine were placed in 5.0 mL DMF. 0.35 g (2.52 mmol) potassium carbonate were added and the mixture was stirred overnight at 60° C. The reaction mixture was poured onto ice water, extracted with ethyl acetate and evaporated down i.vac. The residue was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase was dried and evaporated down i.vac.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionextracted with ethyl acetate
  3. customevaporated down i.vac
  4. customThe residue was purified by chromatography
  5. additionThe fractions containing product
  6. customevaporated down i.vac
  7. customto leave the aqueous residue
  8. extractionextracted with ethyl acetate
  9. customThe organic phase was dried
  10. customevaporated down i.vac

Sources & evidence

ORD record
ord-d8f33325d4c3497bbc2789e879ee069f
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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