Diisopropylethylamine → HCID 22185182, compound

HRID 1795456Notes

Reaction equation

HRID 1795456 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.C(N(C(C)C)CC)(C)C.Cl[C:19]1[N:24]([CH3:25])[C:23](=[O:26])[C:22]([C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)=[C:21]([C:34]2[CH:39]=[CH:38][N:37]=[C:36]([Cl:40])[CH:35]=2)[N:20]=1>ClCCl>[Cl:40][C:36]1[CH:35]=[C:34]([C:21]2[N:20]=[C:19]([N:5]3[CH2:6][CH2:7][CH2:8][CH:4]3[CH2:3][O:2][CH3:1])[N:24]([CH3:25])[C:23](=[O:26])[C:22]=2[C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)[CH:39]=[CH:38][N:37]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 22185212HCID 22185212, compound

Product 1

HCID 22185182HCID 22185182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL RBF, was added (S)-2-methoxymethyl-pyrrolidine (0.172 g, 1.5 mmol), and 50 mL dichloromethane at 0° C. under nitrogen. 0.35 mL diisopropylethylamine (2.0 mmol) was added drop wise, and stirred for 10 min. 2-Chloro-6-(2-chloropyridin-4-yl)-3-methyl-5-m-tolyl-3H-pyrimidin-4-one (0.345 g, 1.0 mmol) was added in one portion, and 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 obtained in 0.40 g as pale yellow solid. MS (ES+): 425 (M+H)+.

Workup

  1. stirringstirred 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-976f43d7ed0c4f8d9e636602b24f0afa
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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