2-Methylbenzimidazole → HCID 59605802, compound

HRID 1945838Notes

Reaction equation

HRID 1945838 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][OH:13])[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.[CH3:20][C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>>[CH3:11][N:8]1[C:7]([CH2:12][OH:13])=[N:6][C:5]2[C:9]1=[N:10][C:2]([N:22]1[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=[C:21]1[CH3:20])=[N:3][C:4]=2[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 119842-MethylbenzimidazoleHCID 71819275HCID 71819275, compound

Product 1

HCID 59605802HCID 59605802, compound

Procedure

(2-Chloro-9-methyl-6-morpholino-9H-purin-8-yl)methanol (4.0 g) was reacted with 2-Methylbenzimidazole (1.96 g) via General Procedure I for Buchwald coupling. The solids were filtered from the reaction mixture while still warm. Water was added to the filtered reaction mixture (5 times the volume of DMF) to precipitate the product out of the reaction mixture. The precipitated orange solid was filtered and dried under vacuum for quantitative yield of (9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methanol.

Workup

  1. filtrationThe solids were filtered from the reaction mixture
  2. temperaturewhile still warm
  3. additionWater was added to the filtered reaction mixture (5 times the volume of DMF)
  4. customto precipitate the product out of the reaction mixture
  5. filtrationThe precipitated orange solid was filtered

Sources & evidence

ORD record
ord-951e326d23dd402bb6ff9870eaa7c5f2
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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