4-methylpyrrolidin-2-one → HCID 22027870, compound

HRID 1791136Notes

Reaction equation

HRID 1791136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22]C([O-])(C)C.[Na+].C[CH:29]1[CH2:33][NH:32][C:31](=[O:34])[CH2:30]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:32]4[CH:33]([CH3:22])[CH2:29][CH2:30][C:31]4=[O:34])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 5339204-methylpyrrolidin-2-oneHCID 9905031N-(3-chlorophenyl)-4-(2-chloropyridin-4-yl)pyrimidin-2-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 22027870HCID 22027870, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

In a Schlenk tube (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.95 g), NaOtBu (0.29 g), dppf (0.1 g), Pd(OAc)2 (0.01 g) and 4-methylpyrrolidin-2one (0.2 g) are added: Three consecutive cycles of vacuum/argon are applied. Thereafter, 10 ml of degassed dioxane is added and the solution is heated to 120° C. (external temperature) for 8 hours. The solvent is removed under vacuum and the crude product is purified over column chromatography (eluent; EE/MeOH=9/1) yielding the title compound, m.p. 162–164° C.

Workup

  1. customThe solvent is removed under vacuum
  2. customthe crude product is purified over column chromatography (eluent; EE/MeOH=9/1)

Sources & evidence

ORD record
ord-093ba01bce4f43b0bc7ec98e3643815d
Source dataset
uspto-grants-2006_07
Patent number
US07074787B2

Reaction notes

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