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Benzimidazole → 2-chloro-6-[6-(phenylmethoxy)-1H-benzimidazol-1-yl]-9-[[2-(trimethylsilyl) ethoxy]methyl]-9H-purine

HRID 1453579
Notes
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Reaction equation

HRID 1453579 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4](Cl)[N:3]=1.[C:20]1([CH2:26][O:27][C:28]2[CH:36]=[CH:35][C:31]3[NH:32][CH:33]=[N:34][C:30]=3[CH:29]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC1C=CC=CC=1)C1C=CC=CC=1.N1C2C=CC=CC=2NC=1>C(O)CCC>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([N:34]2[C:30]3[CH:29]=[C:28]([O:27][CH2:26][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:36]=[CH:35][C:31]=3[N:32]=[CH:33]2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5798BenzimidazoleHCID 7657Dibenzyl etherHCID 582852322,6-Dichloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purineHCID 178420378HCID 178420378, compound

Product 1

HCID 866141022-chloro-6-[6-(phenylmethoxy)-1H-benzimidazol-1-yl]-9-[[2-(trimethylsilyl) ethoxy]methyl]-9H-purineYield 48.8%

Reagents, catalysts & solvents

1
HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

860 mg of product obtained in stage 1 above are mixed with 605 mg of 5-(phenylmethoxy)-1H-benzimidazole (benzyl ether in the 5-position of benzimidazole) and 15 ml of butanol. The mixture is heated at 120° C. for 24 hours. Partial drying, washing with H2O and then drying under vacuum at 50° C. are carried out. 667 mg of 2-chloro-6-[6-(phenylmethoxy)-1H-benzimidazol-1-yl]-9-[[2-(trimethylsilyl)ethoxy]methyl]-9H-purine are obtained, in the form of beige-colored crystals.

Workup

  1. customPartial drying
  2. washwashing with H2O
  3. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-f128de6f5f6748459fc36bcee54d9c29
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07476670B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes