Pyrrolidine → HCID 10369797, compound

HRID 750866Notes

Reaction equation

HRID 750866 reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:7]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[N:6]=1)(=O)=O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>C1COCC1>[N:35]1([C:5]2[N:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=3)[C:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:7]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[N:6]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 10392549HCID 10392549, compound

Product 1

HCID 10369797HCID 10369797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a sealed tube fitted with a magnetic stirrer bar was added 2-methylsulfonyl-4-(3,4-difluorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (from Example 20) (30 mg, 0.06 mmol), 10 eq. of pyrrolidine and THF, flushed with nitrogen. The reaction was heated at 60° C. overnight in the sealed tube. The solvent was removed under reduced pressure. Flash column chromatography on silica gel (eluted with 90/10 hexanes/ethyl acetate) afforded the title compound: HPLC/MS: m/e=532 (M++1); Rt=4.9 min. 1H-NMR 500 MHz (CDCl3): 1.91-2.00 (m, 4H), 3.23-3.40 (s, 2H1), 3.45-3.62 (s, 2H), 6.89-6.94 (m, 1H), 7.08-7.21 (m, 8H), 7.35 (s, 1H).

Workup

  1. customTo a sealed tube fitted with a magnetic stirrer bar
  2. customflushed with nitrogen
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-426e7264e3df4b4fbf21abfb49edee19
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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