Morpholine → (R)-3-(5-methyl-4-morpholino-6-(tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenol

HRID 527465Notes

Reaction equation

HRID 527465 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([NH:9][C@@H:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[N:5]=[C:4]([C:15]2[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[N:3]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[CH3:8][C:7]1[C:2]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:3][C:4]([C:15]2[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)=[N:5][C:6]=1[NH:9][C@@H:10]1[CH2:14][CH2:13][O:12][CH2:11]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 90426130HCID 90426130, compound

Product 1

HCID 90426357(R)-3-(5-methyl-4-morpholino-6-(tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenolYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (R)-3-(4-chloro-5-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenol (800 mg, 2.6 mmol); neat morpholine (274 mg, 3.1 mmol) and Na2CO3 (556 mg, 5.2 mmol) in EtOH (12 mL) was stirred at 80° C. in a sealed vial for 14 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/2 to 2/1) to give the (R)-3-(5-methyl-4-morpholino-6-(tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenol (120 mg, 13% yield) as a light yellow solid. ESI-LCMS (m/z): 357.1 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/2 to 2/1)

Sources & evidence

ORD record
ord-b7dc90f701c94d3581188302502865c6
Source dataset
uspto-grants-2016_05
Patent number
US09346802B2

Reaction notes

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