Water → HCID 59404996, compound

HRID 2387984Notes

Reaction equation

HRID 2387984 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:19])[NH:8][C:9]3[CH:16]=[C:15]([Cl:17])[C:14](I)=[CH:13][C:10]=3[C:11]=2[N:12]=1.[CH2:20]([N:23]([CH3:25])[CH3:24])[C:21]#[CH:22].O>C(N(CC)CC)C.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:19])[NH:8][C:9]3[CH:16]=[C:15]([Cl:17])[C:14]([C:22]#[C:21][CH2:20][N:23]([CH3:25])[CH3:24])=[CH:13][C:10]=3[C:11]=2[N:12]=1

Participants

8

Reactant 3

HCID 962WaterHCID 81643N,N-DimethylpropargylamineHCID 59405025HCID 59405025, compound

Product 1

HCID 59404996HCID 59404996, compoundYield 109.8%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2-amino-9-chloro-10-iodo-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1.66 g, 4.29 mmol) and propargyl(dimethylamine) (0.74 mL, 6.89 mmol) in triethylamine (7 mL) and DMF (7 mL) was degassed with argon. To this solution was added bis(triphenylphosphine)palladium(II) chloride (0.30 g, 0.43 mmol) and copper iodide (0.163 g, 0.86 mmol). The reaction mixture was allowed to stir at 75° C. overnight. After the reaction mixture was allowed to cool to rt, water was added. The precipitate that formed was filtered and dried to give 2-amino-9-chloro-10-[3-(dimethylamino)prop-1-yn-1-yl]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (1.61 g, 98%) as a brown solid. LCMS (FA): m/z=342 (M+H).

Workup

  1. temperatureto cool to rt
  2. customThe precipitate that formed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-5022eda98cbc42909f57b09f2da21e78
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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