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

HRID 1846457Notes

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

Participants

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

extractionextracted several times with EtOAc
customThe combined organic phases were dried on sodium sulphate
customevaporated down
custompurified by preparative HPLC-MS
customthe acetonitrile was evaporated down
extractionextracted with EtOAc
customThe organic phase was dried on sodium sulphate
filtrationfiltered
customevaporated down
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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