Hydrochloric Acid → 4-Chloro-5-methyl-6-(piperidin-4-ylsulfanyl)-pyrimidine

HRID 1036829Notes

Reaction equation

HRID 1036829 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[C:20]([CH3:21])=[C:19]([Cl:22])[N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:22][C:19]1[C:20]([CH3:21])=[C:15]([S:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865973684-(6-Chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 860222804-Chloro-5-methyl-6-(piperidin-4-ylsulfanyl)-pyrimidineYield 114.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(6-chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (2.3469 g, 6.82 mmol) and 40 mL of 4M HCl in dioxane was stirred at room temperature over night. Mixture was concentrated to give 4-chloro-5-methyl-6-(piperidin-4-ylsulfanyl)-pyrimidine as a yellowish solid (1.8985 g, 99%). Exact mass calculated for C10H14ClN3S 243.06, found 244.1 (MH+).

Workup

  1. concentrationMixture was concentrated

Sources & evidence

ORD record
ord-b7cdf96cfb0e40a880300dcf0105c9c4
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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