Sodium hydride → HCID 63867703, compound

HRID 217602Notes

Reaction equation

HRID 217602 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Br:10][C:11]1[CH:12]=[N:13][C:14](Cl)=[N:15][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Br:10][C:11]1[CH:12]=[N:13][C:14]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 766463-(Dimethylamino)-1-propanolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 63867703HCID 63867703, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(dimethylamino)-1-propanol (47, 3.45 mL, 2.84 mmol) in 10 mL of dry tetrahydrofuran, sodium hydride (0.0784 g, 3.10 mmol) was added at room temperature. After 15 minutes, 5-bromo-2-chloro-pyrimidine (46, 0.500 g, 2.58 mmol) was added and the mixture was stirred at room temperature for 16 hours. To this, ˜500 μL of saturated ammonium chloride was added and the reaction was treated with ethyl acetate and filtered. The solvents were removed from the filtrate under vacuum, then added diethyl ether, removed solvent under vacuum and repeated twice. The resulting residue was taken up with tetrahydrofuran/acetonitrile and filtered. Silica gel was added to the filtrate and solvents removed under vacuum, then purified by silica gel chromatography eluting with 1 to 6% methanol in dichloromethane, followed with 20% methanol in dichloromethane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (48, 259 mg). MS (ESI) [M+H+]+=261.9.

Workup

  1. filtrationfiltered
  2. customThe solvents were removed from the filtrate under vacuum
  3. customadded diethyl ether, removed solvent under vacuum
  4. filtrationfiltered
  5. additionSilica gel was added to the filtrate and solvents
  6. customremoved under vacuum
  7. custompurified by silica gel chromatography
  8. washeluting with 1 to 6% methanol in dichloromethane
  9. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-3607cedb475a4aa0bb78e0b8724a936f
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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