Diisopropylethylamine → 5-(3-Bromo-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795451Notes

Reaction equation

HRID 1795451 reaction equation
[CH:1]([NH:4][CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:20][C:21]1[CH:22]=[C:23]([C:27]2[C:28](=[O:41])[N:29]([CH3:40])[C:30](Cl)=[N:31][C:32]=2[C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH:24]=[CH:25][CH:26]=1>ClCCl>[Br:20][C:21]1[CH:22]=[C:23]([C:27]2[C:28](=[O:41])[N:29]([CH3:40])[C:30]([N:7]3[CH2:8][CH2:9][CH2:10][CH:6]3[CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])=[N:31][C:32]=2[C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11564489(R)-isopropyl-pyrrolidin-2-ylmethyl-amineHCID 221851865-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 221851765-(3-Bromo-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL RBF, was added (R)-isopropyl-pyrrolidin-2-ylmethyl-amine (0.78 g, 3.6 mmol), and 50 mL dichloromethane at 0° C. under nitrogen. 2.1 mL diisopropylethylamine (12 mmol) was added drop wise, and stirred for 10 min. 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (1.13 g, 3 mmol) was added in one portion. The mixture was stirred at 0° C. to rt for 12 h. The mixture was diluted with 100 mL dichloromethane, washed with sat. NaHCO3 and brine. After purified by flash chromatography, the title compound was yielded in 1.3 g as pale yellow solid. MS (ES+): 482 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 0° C. to rt for 12 h
  2. washwashed with sat. NaHCO3 and brine
  3. customAfter purified by flash chromatography

Sources & evidence

ORD record
ord-ec7c9279f1b340ce8133c24fe28b95f6
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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