Methyl iodide → 1-methyl-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinone

HRID 706016Notes

Reaction equation

HRID 706016 reaction equation
ClC1C=CC(OC2C=CC(CCO[C:18]3[NH:19][CH:20]=[C:21]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[N:30][CH:31]=4)[C:22](=[O:24])[N:23]=3)=CC=2)=CC=1C(F)(F)F.[CH3:36]CN(C(C)C)C(C)C.CI>ClCCl>[CH3:36][N:19]1[CH:20]=[C:21]([CH2:25][C:26]2[CH:31]=[N:30][CH:29]=[N:28][CH:27]=2)[C:22](=[O:24])[N:23]=[CH:18]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178518457HCID 178518457, compound

Product 1

HCID 679601771-methyl-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinoneYield 43.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]oxy}-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinone (45 mg, 0.089 mmol) in dichloromethane (DCM) (2 mL) was added DIPEA (0.031 mL, 0.179 mmol) and MeI (8.39 μL, 0.134 mmol). The mixture was purified by reverse phase biotage affording 2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy})phenyl)ethyl]oxy}-1-methyl-5-(5-pyrimidinylmethyl)-4(1H)-pyrimidinone (20 mg, 0.039 mmol, 43.2% yield) LCMS: rt=3.37 min, [M+H+]=517

Workup

  1. customThe mixture was purified by reverse phase biotage

Sources & evidence

ORD record
ord-09d32227497c4e25ab3b929d893f077e
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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