Pyrrolidine → Methyl 2-(4-methyl-2-(pyrrolidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

HRID 1399597Notes

Reaction equation

HRID 1399597 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17][CH3:18])=[O:16])=[C:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:8]=1>O1CCCC1>[CH3:13][C:11]1[C:10]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17][CH3:18])=[O:16])=[C:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:8]=[C:7]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:12]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50996613Methyl 2-(4-methyl-2-(pyrrolidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-methyl-2-(pyrrolidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate was prepared according to the general method A starting from pyrrolidine (0.111 mL; 1.32 mmol) and methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.110 g; 0.264 mmol) in tetrahydrofuran (2 mL). Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-20%) in heptane furnished 90 mg (93%) of the title compound as an oil. ESI/APCI(+): 368 (M+H), 390 (M+Na). ESI/APCI(−): 366 (M−H).

Workup

  1. customMethyl 2-(4-methyl-2-(pyrrolidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-20%) in heptane

Sources & evidence

ORD record
ord-05e9ebbaf5dc41aebcbf1c8557b8b72c
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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