Imidazole → 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870596Notes

Reaction equation

HRID 870596 reaction equation
[H-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27]Cl)=[O:23])[CH2:19][C:17]=2[N:18]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C)C=O.ClCCl>[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[CH2:21][N:20]([C:22]([O:24][CH2:25][CH2:26][CH2:27][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[O:23])[CH2:19][C:17]=2[N:18]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

Product 1

HCID 867265613-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylateYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Add sodium hydride (0.068 g; 2.25 equiv; 1.70 mmoles) to a solution of: 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (0.283 g; 1.0 equiv; 0.76 mmoles), and 1H-imidazole (0.105 g; 2.0 equiv; 1.54 mmoles) in dimethylformamide (2.4 mL). Stir the reaction mixture for 16 hours, then dilute with dichloromethane and wash with water. Extract the aqueous layer with dichloromethane twice. Concentrate the combined organic extracts and then purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford of 3-(1H-imidazol-1-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (0.0922 g; 30%) as a yellow solid: MS (m/z): 405(M+1).

Workup

  1. washwash with water
  2. extractionExtract the aqueous layer with dichloromethane twice
  3. concentrationConcentrate the combined organic extracts
  4. custompurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c12fbb077c646fbbf6c09a46dd60329
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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