N-methyl-2-pyrrolidone → 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-1,7-dihydro-purin-6-one

HRID 536004Notes

Reaction equation

HRID 536004 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[NH:21][C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17](Cl)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[NH:21][C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 46913081HCID 46913081, compound

Product 1

HCID 671350988-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-1,7-dihydro-purin-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 8-(1-benzyl-1H-pyrazol-4-yl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one (prepared as given in Example 1) (1.2 g, 3.2 mmol), pyrrolidine (0.34 g, 4.8 mmol), Diisopropyl ethyl amine (0.826 g, 6.4 mmol) and N-methylpyrrolidone (12 ml) were heated at 80-90° C. for 20 hours. Reaction mixture was cooled to 20-25° C. and water (20 ml) was added, solid separated out. The solid material was filtered off and purified by column chromatography to get pure 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-1,7-dihydro-purin-6-one as off white solid (0.83 g, 64%).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. customsolid separated out
  4. filtrationThe solid material was filtered off
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-b2c8e6d62b4a4faea1f230357b5e6fd7
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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