Hydrochloric Acid → 8-isopropyl-5-methyl-2-(3-nitro-5-trifluoromethyl-phenylamino)-7,8-dihydro-5H-pteridin-6-one

HRID 1957991Notes

Reaction equation

HRID 1957991 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[CH2:6][N:5]([CH:14]([CH3:16])[CH3:15])[C:4]=2[N:3]=1.[N+:17]([C:20]1[CH:21]=[C:22]([NH2:30])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)([O-:19])=[O:18].Cl>O.O1CCOCC1>[CH:14]([N:5]1[C:4]2[N:3]=[C:2]([NH:30][C:22]3[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7](=[O:13])[CH2:6]1)([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27757093-Nitro-5-(trifluoromethyl)anilineHCID 584059002-chloro-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one

Product 1

HCID 684223458-isopropyl-5-methyl-2-(3-nitro-5-trifluoromethyl-phenylamino)-7,8-dihydro-5H-pteridin-6-oneYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one of (2 g; 8.30 mmol) and 3-nitro-5-trifluoromethyl-phenylamine (1.71 g; 8.30 mmol) were diluted in 10 ml of water and 10 ml of 1,4-dioxane. 2 ml of HCl 37% were added. The reaction mixture was refluxed 48 h, then cooled to room temperature. The desired product precipitated from the reaction mixture, so, it was filtered, washed with water and dried in vacuo. Recrystallisation with 1,4-dioxane/water 1:1 gave 1.65 g (4.04 mmol; 49% yield) of white-yellow powder.

Workup

  1. temperatureThe reaction mixture was refluxed 48 h
  2. customThe desired product precipitated from the reaction mixture
  3. filtrationso, it was filtered
  4. washwashed with water
  5. customdried in vacuo
  6. customRecrystallisation with 1,4-dioxane/water 1:1
  7. customgave 1.65 g (4.04 mmol; 49% yield) of white-yellow powder

Sources & evidence

ORD record
ord-31c959b9d76542829d67c3f973ab4e2f
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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