2-Methylbenzimidazole → HCID 59593144, compound

HRID 2098673Notes

Reaction equation

HRID 2098673 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:17][C:18]1[NH:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>O>[CH3:17][C:18]1[N:22]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]=1

Participants

4

Reactant 2

HCID 119842-MethylbenzimidazoleHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine

Product 1

HCID 59593144HCID 59593144, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (155 mg) and 2-methylbenzimidazole (161 mg) were heated together at 135° C. overnight. The mixture was then cooled, diluted with water and extracted with ethyl acetate. Combined extracts were dried (Na2SO4), filtered and concentrated. Flash chromatography followed by trituration gave 174 (28%). NMR: (CDCl3): 2.95 (s, 3H, CH3), 3.89-3.91 (m, 4H, 2×CH2), 4.07-4.09 (m, 4H, 2×CH2), 7.25-7.28 (m, 2H, 2× ArH), 7.50 (d, H, ArH, J=5.47 Hz), 7.71 (m, H, ArH), 7.85 (d, H, ArH, J=5.48 Hz), 8.09 (m, H, ArH). MS: (ESI+): MH+=352.13

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85abb5a500f049d6ba2f0c8d2e9ad5c6
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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