1,1'-Carbonyldiimidazole → HCID 86726572, compound

HRID 870608Notes

Reaction equation

HRID 870608 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH:13]1[C:17]([CH2:18][CH2:19][CH2:20][OH:21])=[CH:16][N:15]=[CH:14]1.O.Cl.Cl.[CH2:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]1[NH:34][C:35]1[N:36]=[CH:37][C:38]2[CH2:43][NH:42][CH2:41][C:39]=2[N:40]=1>CN(C)C=O>[CH2:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH:26]1[NH:34][C:35]1[N:36]=[CH:37][C:38]2[CH2:43][N:42]([C:1]([O:21][CH2:20][CH2:19][CH2:18][C:17]3[NH:13][CH:14]=[N:15][CH:16]=3)=[O:2])[CH2:41][C:39]=2[N:40]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5727003-(1H-Imidazol-4-yl)-1-propanolHCID 86726534N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate

Product 1

HCID 86726572HCID 86726572, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Add 1,1′-carbonyldiimidazole (0.51 g; 1.2 equiv; 3.15 mmoles) to a solution of 3-(1H-imidazol-5-yl)propan-1-ol (0.50 g; 1.0 equiv; 2.62 mmoles) in dimethylformamide (8.5 mL) and stir for 1 hour. Slowly add N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate (0.94 g; 1.10 equiv; 2.89 mmoles) to the aforementioned solution. Stir for 16 hours at ambient temperature and then heat to 60° C. for an additional 16 hours. Partition the reaction mixture between water and chloroform and separate the layers. Further extract the aqueous layer with chloroform (2×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to a viscous liquid. Purify the crude product by column chromatography (0 to 20% methanol in dichloromethane) to afford 3-(1H-imidazol-5-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.041 g; 4%) as a brown solid: MS (m/z): 405(M+1).

Workup

  1. stirringStir for 16 hours at ambient temperature
  2. customPartition the reaction mixture between water and chloroform
  3. customseparate the layers
  4. extractionFurther extract the aqueous layer with chloroform (2×)
  5. dry with materialDry the combined organic extracts over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to a viscous liquid
  8. customPurify the crude product by column chromatography (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1d1ddd28953a422bb1b045be171b3f14
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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