Sodium hydride → Tert-butyl 3-((5-aminopyrimidin-4-yl)oxy)pyrrolidine-1-carboxylate

HRID 1528140Notes

Reaction equation

HRID 1528140 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl[C:17]1[C:22]([NH2:23])=[CH:21][N:20]=[CH:19][N:18]=1>O1CCCC1>[NH2:23][C:22]1[C:17]([O:15][CH:12]2[CH2:13][CH2:14][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11]2)=[N:18][CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 44169391-Boc-3-pyrrolidinolHCID 134045414-Chloropyrimidin-5-amine

Product 1

HCID 86720863Tert-butyl 3-((5-aminopyrimidin-4-yl)oxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

At room temperature, NaH (71 mg, 2.94 mmol) was added to a solution of tert-butyl-3-hydroxypyrrolidine-1-carboxylate (1B2) (500 mg, 2.67 mmol) in THF (tetrahydrofuran) (10 mL) and stirred for 1 hour. 4-chloropyrimidin-5-amine (H) (348 mg, 2.67 mmol) was then added. The reaction mixture was then heated to 100° C. under nitrogen and stirred for 4 hours, cooled to room temperature (20-30° C.) and concentrated in vacuo. The residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether) to obtain the product 1D3 (336 mg, 1.2 mmol).

Workup

  1. stirringstirred for 4 hours
  2. temperaturecooled to room temperature (20-30° C.)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether)
  5. customto obtain the product 1D3 (336 mg, 1.2 mmol)

Sources & evidence

ORD record
ord-969267a84497407caaa7e4c83b1e3917
Source dataset
uspto-grants-2015_07
Patent number
US09090594B2

Reaction notes

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