2-Methyl-3-butyn-2-ol → HCID 69286462, compound

HRID 2057057Notes

Reaction equation

HRID 2057057 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH:18]([CH3:20])[CH3:19])[N:14]=[C:13]([O:21][C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(CC)CC)C.[CH3:36][C:37]([OH:41])([C:39]#[CH:40])[CH3:38]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[NH:10][C:11]1[N:16]=[C:15]([NH:17][CH:18]([CH3:20])[CH3:19])[N:14]=[C:13]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:40]#[C:39][C:37]([CH3:38])([OH:41])[CH3:36])[N:12]=1

Participants

8

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 59659974HCID 59659974, compound

Product 1

HCID 69286462HCID 69286462, compoundYield 70.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of compound N-(3-Chloro-4-methoxy-phenyl)-6-(4-iodo-phenoxy)-N′-isopropyl-[1,3,5]triazine-2,4-diamine (0.4 g, 0.78 mmol), triethylamine (0.27 ml, 1.95 mmol) in dimethylformamide (3 mL) was added bis(triphenylphosphine)palladium(II)chloride (27 mg, 0.04 mmol), CuI (15 mg, 0.08 mmol) and 2-methyl-3-butyn-2-ol (0.11 ml, 1.17 mmol). It is stirred under nitrogen atmosphere for 6 hrs. The mixture was then cooled, diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography (10-20% EtOAc-Hexane) to afford the title compound as a pale yellow solid (0.256 g, 70%). mp 138-140° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 254 nm, Rt 16.80 min, 97.77% purity; MS (CI): m/z 468 (M+H, 100).

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with water (2×10 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (10-20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-ec4966660d7c437f941890a121a25f26
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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