Water → HCID 63867546, compound

HRID 1916569Notes

Reaction equation

HRID 1916569 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[Br:11][C:12]1[CH:13]=[N:14][C:15](Cl)=[N:16][CH:17]=1.O>C1COCC1>[Br:11][C:12]1[CH:13]=[N:14][C:15]([O:3][CH2:4][CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 63867546HCID 63867546, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50 mg (1.15 mmol, 60%) NaH are added to a solution of 0.17 mL (1.38 mmol) N-(2-hydroxyethyl)pyrrolidine in 10 mL THF at RT. The reaction solution is stirred for 15 min at RT and then 200 mg (1.03 mmol) 5-bromo-2-chloropyrimidine are added. The solution is stirred for 16 h at RT. 10 mL water are added and the aqueous phase is extracted with 20 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (DCM/MeOH/NH3 9:1:0.1).

Workup

  1. stirringThe solution is stirred for 16 h at RT
  2. extractionthe aqueous phase is extracted with 20 mL EtOAc
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customFurther purification

Sources & evidence

ORD record
ord-5e05170c2e294bd9b34ead06234b3776
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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