2-Bromopropane → HCID 57761324, compound

HRID 230969Notes

Reaction equation

HRID 230969 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)[N:12]=[C:11]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].Br[CH:38]([CH3:40])[CH3:39].[BH4-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)[N:12]=[C:11]([C:31]3[CH2:36][CH2:35][N:34]([CH:38]([CH3:40])[CH3:39])[CH2:33][CH:32]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 4311764Sodium borohydrideHCID 57761720HCID 57761720, compound

Product 1

HCID 57761324HCID 57761324, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Dissolve 4-(3-chloro-4-fluorophenyl)-6-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-2-(pyridin-4-yl)pyrimidine (40 mg) and 2-bromopropane (0.1 mL) in DMF (1.5 mL) under nitrogen atmosphere. Heat the mixture in a sealed tube at 120° C. for 48 hours. Cool the mixture to room temperature and then add NaBH4 (50 mg). Stir the mixture at room temperature for 20 hours, dilute with water (5 mL), extract with EtOAc (3×3 mL) and dry over MgSO4. Filter, and concentrate under vacuum to afford crude product and purify by flash column chromatography using 20% EtOAc/hexane to afford the title product as white solid. Mass spec m/z=561.27.

Workup

  1. temperatureCool the mixture to room temperature
  2. extractionextract with EtOAc (3×3 mL)
  3. dry with materialdry over MgSO4
  4. filtrationFilter
  5. concentrationconcentrate under vacuum
  6. customto afford crude product
  7. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-9be5ffe8684b49269ab57f9ce737d3c0
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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