4-(2,6-Dichloropyrimidin-4-yl)morpholine → 4-Chloro-2-(4-ethoxy-4-oxo-butyl)-6-morpholinopyrimidine

HRID 1830518Notes

Reaction equation

HRID 1830518 reaction equation
[Br-].[CH2:2]([O:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][Zn+])[CH3:3].Cl[C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[C:14]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:13]=1>C1COCC1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[Cl:18][C:16]1[CH:15]=[C:14]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:13]=[C:12]([CH2:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:10])[N:17]=1

Participants

5

Reactant 2

HCID 115866994-(2,6-Dichloropyrimidin-4-yl)morpholineHCID 178471550HCID 178471550, compound

Product 1

HCID 220469094-Chloro-2-(4-ethoxy-4-oxo-butyl)-6-morpholinopyrimidineYield 33%

Reagents, catalysts & solvents 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-ethoxy-4-oxo-butylzinc bromide (50 mL 0.5M in THF, 25 mmol), 2,4-dichloro-6-morpholinopyrimidine (4.68 g, 20.0 mmol) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (0.15 g, 0.2 mmol) in THF (total volume 80 mL) was stirred at 60° C. for 2 days. After routine workup, flash chromatography purification was performed to obtain 4-chloro-2-(4-ethoxy-4-oxo-butyl)-6-morpholinopyrimidine as a white solid (2.073 g, 6.60 mmol, 33.0%).

Workup

  1. customAfter routine workup, flash chromatography purification

Sources & evidence

ORD record
ord-61c77f89da43486d8f0d144894debdd1
Source dataset
uspto-grants-2006_06
Patent number
US07067514B2

Reaction notes

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