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Potassium Carbonate → 6-(6-chloro-pyrimidin-4-yloxy)-2,4-dimethyl-1H-benzimidazole

HRID 1846457
Notes
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Reaction equation

HRID 1846457 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[CH:10][N:9]=1.[CH3:15][C:16]1[NH:17][C:18]2[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([CH3:26])[C:19]=2[N:20]=1>CN(C=O)C>[Cl:14][C:12]1[N:11]=[CH:10][N:9]=[C:8]([O:25][C:23]2[CH:22]=[C:21]([CH3:26])[C:19]3[N:20]=[C:16]([CH3:15])[NH:17][C:18]=3[CH:24]=2)[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 669782362,7-dimethyl-3H-benzimidazol-5-ol

Product 1

HCID 866639086-(6-chloro-pyrimidin-4-yloxy)-2,4-dimethyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.66 g (12.0 mmol) potassium carbonate were added to 0.676 g (4.40 mmol) 4,6-dichloropyrimidine and 0.649 g (4.00 mmol) 2,7-dimethyl-3H-benzimidazol-5-ol in 5.00 mL DMF and stirred for 8 h at 50° C. Then the mixture was added to ice water and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, evaporated down and purified by preparative HPLC-MS. The product-containing fractions were combined and the acetonitrile was evaporated down. The residue was made alkaline with 1N aqueous sodium hydroxide solution and extracted with EtOAc. The organic phase was dried on sodium sulphate, filtered, evaporated down and dried under HV.

Workup

  1. extractionextracted several times with EtOAc
  2. customThe combined organic phases were dried on sodium sulphate
  3. customevaporated down
  4. custompurified by preparative HPLC-MS
  5. customthe acetonitrile was evaporated down
  6. extractionextracted with EtOAc
  7. customThe organic phase was dried on sodium sulphate
  8. filtrationfiltered
  9. customevaporated down
  10. customdried under HV

Sources & evidence

ORD record
ord-8f6bf65edbc94931a187a2a471cdfa2b
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952014B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes