Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → 2-Amino-4-chloro-5-(2,4-dichlorophenyl)-6-methylthio pyrimidine

HRID 846367Notes

Reaction equation

HRID 846367 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4](Cl)[N:3]=1.[Na].[CH3:19][SH:20].COCCOCCN(CCOCCOC)CCOCCOC>[Cu].C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([S:20][CH3:19])[N:3]=1

Participants

6

Reactant 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 197050544,6-Dichloro-5-(2,4-dichlorophenyl)pyrimidin-2-amineHCID 45051789Methylmercaptan sodium

Product 1

HCID 197050792-Amino-4-chloro-5-(2,4-dichlorophenyl)-6-methylthio pyrimidineYield 52%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-5-(2,4-dichlorophenyl)-4,6-dichloropyrimidine (0.5 g) (Example 32) THF (15 ml), methanethiol sodium salt (0.113 g), copper powder (0.05 g) and tris[2-(2-methoxyethoxy)ethyl]amine (0.1 g) was heated in an autoclave at 180° C. for 18 hours. The cooled reaction mixture was filtered, evaporated and the residue purified by flash column chromatography to give the title compound (0.262 g, 52%), mp. 201°-202° C. (softens at 196° C.).

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-f168b3f90bc04c31b3e9c274af93aad9
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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