1,1'-Carbonyldiimidazole → HCID 57425936, compound

HRID 1363140Notes

Reaction equation

HRID 1363140 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][O:14][C:15]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:16]=1[CH2:17][NH:18][C:19]1[N:24]=[C:23]([NH:25][CH2:26][C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[F:34])[C:22]([NH2:35])=[CH:21][N:20]=1>C1COCC1>[CH3:13][O:14][C:15]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:16]=1[CH2:17][NH:18][C:19]1[N:24]=[C:23]2[C:22]([NH:35][C:1](=[O:2])[N:25]2[CH2:26][C:27]2[C:28]([F:34])=[CH:29][CH:30]=[CH:31][C:32]=2[F:33])=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59727003HCID 59727003, compound

Product 1

HCID 57425936HCID 57425936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (0.93 g) was added to a solution of N2-(2,4-dimethoxybenzyl)-N4-(2,6-difluorobenzyl)pyrimidine-2,4,5-triamine (54) in THF (20 mL) and the resultant mixture stirred at RT overnight, then the solvents were removed under reduced pressure and the taken up in EtOAc and washed trice with water. The organics were dried, filtered and evaporated and purified via column chromatography, elution with 2.5 and 4% MeOH/DCM, to yield 2-(2,4-Dimethoxybenzylamino)-9-(2,6-difluorobenzyl)-7H-purin-8(9H)-one (55) (0.58 g), MH+=428.

Workup

  1. customthe solvents were removed under reduced pressure
  2. washwashed trice with water
  3. customThe organics were dried
  4. filtrationfiltered
  5. customevaporated
  6. custompurified via column chromatography, elution with 2.5 and 4% MeOH/DCM

Sources & evidence

ORD record
ord-cb0741bb3d9043df8b99fb4d685f837f
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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