HCID 53752050, compound → HCID 23512644, compound

HRID 354017Notes

Reaction equation

HRID 354017 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[CH:13][N:12]=[C:11]([S:22][CH3:23])[N:10]=1)C)(C)(C)C>CO.Cl>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]1[C:9]([NH:7][CH3:6])=[N:10][C:11]([S:22][CH3:23])=[N:12][CH:13]=1

Participants

3

Reactant 1

HCID 53752050HCID 53752050, compound

Product 1

HCID 23512644HCID 23512644, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of 2.40 g (6.5 mmol) [5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-methyl-carbamic acid tert-butyl ester in 30 ml MeOH/HCl (2N) was stirred at 55° for 3 hrs. After evaporation of the solvent, the residue was distributed between 40 ml 1N NaOH and 40 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 50 ml CH2C2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1) to give 1.70 g (97%) [5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-methyl-amine as a white solid, MS (EI): 265 (M+).

Workup

  1. customAfter evaporation of the solvent
  2. customThe phases were separated
  3. washthe aqueous layer washed twice with 50 ml CH2C2
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-924945d52a724786b5524169c81ccafc
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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