Triethylamine → 4-(7-Hydroxy-6-((trimethylsilyl)ethynyl)quinazolin-2-ylamino)-N-isopropylbenzamide

HRID 2079646Notes

Reaction equation

HRID 2079646 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([NH:13][C:14]1[CH:25]=[CH:24][C:17]([C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1)[N:6]=[CH:5]2.C(N(CC)CC)C.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35]>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[OH:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[N:6][C:7]([NH:13][C:14]3[CH:25]=[CH:24][C:17]([C:18]([NH:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=3)=[N:8]2)=[CH:3][C:2]=1[C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 1360299224-(6-Bromo-7-hydroxyquinazolin-2-ylamino)-N-isopropylbenzamide

Product 1

HCID 1363604854-(7-Hydroxy-6-((trimethylsilyl)ethynyl)quinazolin-2-ylamino)-N-isopropylbenzamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0.09M mixture of 4-(6-bromo-7-hydroxyquinazolin-2-ylamino)-N-isopropylbenzamide (0.17 mM), triethylamine (0.5 ml), Pd(dppf)2Cl2CH2Cl2 (0.1 eq), Copper(I) iodide (0.1 eq), in DMF was added trimethylsilylacetylene (10 eq). The suspension was microwaved at 120° C. for 20 min. Reaction mixture was diluted with ethyl acetate and was washed with water, brine, dried and concentrated to give crude product. ES/MS m/z 419 (MH+).

Workup

  1. customThe suspension was microwaved at 120° C. for 20 min
  2. customReaction mixture
  3. washwas washed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product

Sources & evidence

ORD record
ord-51e77951048d4fe59278fdbccbefe0c5
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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