Morpholine → Methyl 2-(4-methyl-2-morpholino-6-p-tolylpyrimidin-5-yl)pentanoate

HRID 1399595Notes

Reaction equation

HRID 1399595 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18][CH3:19])=[O:17])=[C:10]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:9]=1>O1CCCC1>[CH3:14][C:12]1[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18][CH3:19])=[O:17])=[C:10]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:9]=[C:8]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:13]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50996794Methyl 2-(4-methyl-2-morpholino-6-p-tolylpyrimidin-5-yl)pentanoateYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-methyl-2-morpholino-6-p-tolylpyrimidin-5-yl)pentanoate was prepared according to the general method A starting from morpholine (0.107 mL; 1.20 mmol) and methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.100 g; 0.239 mmol) in tetrahydrofuran (2 mL). Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-25%) in heptane furnished 74 mg (81%) of the title compound as an oil. ESI/APCI(+): 384 (M+H).

Workup

  1. customMethyl 2-(4-methyl-2-morpholino-6-p-tolylpyrimidin-5-yl)pentanoate was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-25%) in heptane

Sources & evidence

ORD record
ord-b092cb735b3541f79657f7fbfa5e30b4
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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