2-Chloropyrimidine → HCID 67407141, compound

HRID 1949648Notes

Reaction equation

HRID 1949648 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]2[NH:13][CH2:14][CH:15]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]2[N:13]([C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH2:14][CH:15]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 67408727HCID 67408727, compound

Product 1

HCID 67407141HCID 67407141, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution containing 34 (370 mg, 1.07 mmol), DIPEA (163 mg, 1.26 mmol), and 2-chloropyrimidine (135 mg, 1.17 mmol) in anhydrous DMF (6 mL) was warmed to 70° C. After 16 h, the reaction mixture was cooled to ambient temperature and diluted with water and subsequently extracted with diethyl ether. The organic extract was washed successively with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 210 mg (46%) of 70 as a white solid. Mass spectrum, m/z [424] (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. extractionsubsequently extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed successively with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-503962a6d9854e43924f86420dafda1f
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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