Sodium hydride → 2-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid ethyl ester

HRID 1175375Notes

Reaction equation

HRID 1175375 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[CH2:19]([O:21][C:22](=[O:26])[C@@H:23]([OH:25])[CH3:24])[CH3:20].[H-].[Na+]>C1COCC1>[CH2:19]([O:21][C:22](=[O:26])[C@@H:23]([O:25][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1)[CH3:24])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 92831(L)-ethyl lactateHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 866198752-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The subtitle compound was prepared according to the procedure outlined in example 1 step iii) using 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (product of example 1 step ii) (0.77 g), THF (15 mL), 2-hydroxy-(2S)-propanoic acid ethyl ester (0.40 mL) and 60% sodium hydride (0.14 g) to give the subtitle compound as a clear, colourless oil. Yield: 1 g

Workup

  1. customThe subtitle compound was prepared

Sources & evidence

ORD record
ord-12777d7d5bd64073b93be82ddf7f0ad9
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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