Benzimidazole → HCID 57474742, compound

HRID 391685Notes

Reaction equation

HRID 391685 reaction equation
CO[C:3]([C:5]1[C:10]([N+:11]([O-])=O)=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[N:8]=[C:7]([N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]=[CH:24]2)[N:6]=1)=[O:4].[NH:32]1C2C=CC=CC=2N=C1.[H-].[Na+].ClC1N=C([C:50](OC)=[O:51])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1>O1CCCC1>[N:23]1([C:7]2[N:8]=[C:9]3[C:10]([NH:11][C:50](=[O:51])[N:14]3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:5]([C:3]([NH2:32])=[O:4])[N:6]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1

Participants

6

Reactant 4

HCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 57474738HCID 57474738, compoundHCID 68965458HCID 68965458, compound

Product 1

HCID 57474742HCID 57474742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Methyl-2-(1H-benzo[d]imidazol-1-yl)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. To a solution of 1H-benzo[d]imidazole (0.354 g, 3.0 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (0.120 g, 60% in mineral oil, 30 mmol). The reaction mixture was stirred at 60° C. for 15 min. Methyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (1.014 g, 3 mmol) was added and the resulting solution was stirred for 4 h. The reaction mixture was extracted with EtOAc (3×25 mL) and washed with brine (3×25 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was subjected to silica gel chromatography (25%-40% EtOAc in hexanes). Concentration of the desired fractions afforded the titled compound as yellow solid (1.0 g). MS (ESI) m/z 421.4 [M+1]+.

Workup

  1. stirringthe resulting solution was stirred for 4 h
  2. extractionThe reaction mixture was extracted with EtOAc (3×25 mL)
  3. washwashed with brine (3×25 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c792aee20b0744c7967062e81e3175c3
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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