4-[4-(3-Chloro-6-methoxy-pyridin-2-yl)-2-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine → HCID 178430149, compound

HRID 230959Notes

Reaction equation

HRID 230959 reaction equation
[Cl:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[N:19]=[C:18]([N:29]4[CH2:33][CH2:32][CH2:31][CH:30]4[CH3:34])[N:17]=3)[CH:12]([CH3:35])[CH2:11]2)=[N:4][C:5]([O:8]C)=[CH:6][CH:7]=1>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[N:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[N:19]=[C:18]([N:29]3[CH2:33][CH2:32][CH2:31][CH:30]3[CH3:34])[N:17]=2)[CH:12]([CH3:35])[CH2:11]1

Participants

3

Reactant 1

HCID 688239464-[4-(3-Chloro-6-methoxy-pyridin-2-yl)-2-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

Product 1

HCID 178430149HCID 178430149, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat a solution of 4-[4-(3-chloro-6-methoxy-pyridin-2-yl)-2-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine (120 mg, 0.241 mmol) in concentrated HCl at 90° C. for 24 hours. Cool to room temperature, adjust the pH to 7, and extract with EtOAc. Wash with brine, dry the solution (Na2SO4), and concentrate under reduced pressure. Purify the residue by flash column chromatography eluting with EtOAc:Hexanes (1:4) to afford 5-chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-methyl-piperazin-1-yl}-pyridin-2-ol as an off-white solid. 1H NMR (300 MHz, CDCl3): δ1.32 (m, 6H, 2×CH3); 1.69 (m, 1H, CH2CH2); 1.91 (m, 1H, CH2CH2); 2.04 (m, 2H, CH2CH2); 3.06 (m, 1H); 3.24 (m, 1H); 3.36 (m, 1H); 3.67 (m, 4H); 4.33 (m, 2H); 4.71 (m, 1H); 6.22 (m, 2H); 7.10 (m, 2H); 7.45 (d, J=8.7 Hz, 1H); 8.01 (m, 2H); 9.27 (br, 1H, OH).

Workup

  1. extractionextract with EtOAc
  2. washWash with brine
  3. dry with materialdry the solution (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue by flash column chromatography
  6. washeluting with EtOAc:Hexanes (1:4)

Sources & evidence

ORD record
ord-34090560fef64cbebadefb55b486bd1a
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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