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Ammonia → 2,4-Diamino-6-methyl-5-(2,3,5-trichloro-4-nitrophenyl)pyrimidine

HRID 234923
Notes
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Reaction equation

HRID 234923 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:10]=2[Cl:17])=[C:4]([CH3:18])[N:3]=1.[N+:19]([O-])([O-:21])=[O:20].[K+].N>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[C:13]([Cl:15])[C:12]([N+:19]([O-:21])=[O:20])=[C:11]([Cl:16])[C:10]=2[Cl:17])=[C:4]([CH3:18])[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 115512322,4-Diamino-6-methyl-5-(2,3,5-trichlorophenyl)pyrimidine

Product 1

HCID 233535442,4-Diamino-6-methyl-5-(2,3,5-trichloro-4-nitrophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2,4-Diamino-6-methyl-5-(2,3,5-trichlorophenyl)pyrimidine (0.152 g) (Example 6) was dissolved in concentrated sulphuric acid and potassium nitrate (50 mg) was added. The solution was stirred at room temperature overnight, then poured onto ice and basified with 0.880 ammonia. The product was extracted into ethyl acetate, bulked, dried (MgSO4) and evaporated. The residue was purified by chromatography on SiO2 gel, eluting with EtOAc to 8% MeOH/EtOAc to give the desired product, 0.13 g, mp. 313°-315° C.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography on SiO2 gel
  5. washeluting with EtOAc to 8% MeOH/EtOAc

Sources & evidence

ORD record
ord-7858a4f009744042b8a194d4cb845b59
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05597827

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes