Triethylamine → (R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine

HRID 527463Notes

Reaction equation

HRID 527463 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[C:4](Cl)[N:3]=1.Cl.[O:12]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:3]=[C:4]([NH:17][C@@H:14]2[CH2:15][CH2:16][O:12][CH2:13]2)[C:5]([CH3:9])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2327892,4,6-Trichloro-5-methylpyrimidineHCID 46856371(3R)-3-Aminotetrahydrofuran hydrochloride

Product 1

HCID 90426233(R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amineYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4,6-trichloro-5-methylpyrimidine (2 g, 10.2 mmol), (R)-tetrahydrofuran-3-amine hydrochloride (1.12 g, 9.2 mmol) and Et3N (2.1 g, 20.3 mmol) in EtOH (20 mL) was stirred at room temperature for 14 h., concentrated under vacuum and the residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/0 to 2/1) to give the (R)-2,6-dichloro-5-methyl-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine (1.25 g, 53% yield) as a white solid. ESI-LCMS (m/z): 248.1 [M+1]+.

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue was purified by chromatographic column on silica gel (EtOAc/petroleum ether, gradient elution, from 1/0 to 2/1)

Sources & evidence

ORD record
ord-772f106915e948ccb144b2c781f961a0
Source dataset
uspto-grants-2016_05
Patent number
US09346802B2

Reaction notes

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