Ammonia → 2,4-Diamino-5-(2,4-dichlorophenyl)-6-methylthiopyrimidine

HRID 2292528Notes

Reaction equation

HRID 2292528 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([S:17][CH3:18])[N:3]=1.N.COCCOCC[N:27](CCOCCOC)CCOCCOC>[Cu].CCO>[NH2:1][C:2]1[N:7]=[C:6]([NH2:27])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:4]([S:17][CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 197050792-Amino-4-chloro-5-(2,4-dichlorophenyl)-6-methylthio pyrimidine

Product 1

HCID 197051172,4-Diamino-5-(2,4-dichlorophenyl)-6-methylthiopyrimidineYield 1,181.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-4-chloro-5-(2,4-dichlorophenyl)-6-methylthio pyrimidine (0.5 g) (Example 32) EtOH saturated with ammonia (20 ml), copper powder (0.05 g) and tris[2-(2-methoxyethoxy)ethyl]amine (0.01 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 (0.11 g, 23.5%), mp. 191°-192° C. Microanalysis:

Workup

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

Sources & evidence

ORD record
ord-f87ed0efc4b54e45b41404fda0258dd7
Source dataset
uspto-grants-1997_11
Patent number
US05684005

Reaction notes

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