2,4-Dichloro-6-phenyl-1,3,5-triazine → HCID 178478385, compound

HRID 855659

Reaction equation

HRID 855659 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:9])[NH:7][N:8]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[N:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:12]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:10][C:11]1[N:12]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=[C:15]([NH:9][C:6]2[NH:7][N:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:5]=2)[N:16]=1

Participants

5

Reactant 3

HCID 155492,4-Dichloro-6-phenyl-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 178507266HCID 178507266, compound

Product 1

HCID 178478385HCID 178478385, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-cyclopropyl-2H-pyrazol-3-ylamine (172 mg, 1.4 mmol) in 5 ml of THF was added dropwise to a solution of 2,4-dichloro-6-phenyl-[1,3,5]triazine (452 mg, 2 mmol) (ref: WO 0125220, p.190) and diisopropylethylamine (0.35 ml, 2 mmol) in 15 ml of THF at room temperature then stirred for 18 hours. The reaction was filtered and the filtrate evaporated in vacuo and the residue purified by flash chromatography (SiO2) eluting with 8:2 dichloromethane: ethyl acetate to afford 233 mg of the desired product. HPLC: Rt 6.803 mins. MS: m/z 313.0 (M+H)

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated in vacuo
  3. customthe residue purified by flash chromatography (SiO2)
  4. washeluting with 8:2 dichloromethane

Sources & evidence

ORD record
ord-55b006ba5e8b4cc99467659b773b61bc
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Linked notes

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