Triphenylphosphine → 4-chloro-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline

HRID 916396Notes

Reaction equation

HRID 916396 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:46][N:47]([CH2:51][CH2:52]O)[CH2:48][C:49]#[CH:50]>C(Cl)Cl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:52][CH2:51][N:47]([CH3:46])[CH2:48][C:49]#[CH:50])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2879292-[Methyl(prop-2-yn-1-yl)amino]ethan-1-olHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 589602564-chloro-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazolineYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (0.297 g, 1.71 mmol) was added to a solution of 4-chloro-7-hydroxy-6-methoxyquinazoline (0.3 g, 1.42 mmol), (prepared as described for the starting material in Example 4), triphenylphosphine (0.485 g, 1.85 mmol) and 2-(N-methyl-N-prop-2-yn-1-ylamino)ethanol (0.177 g, 1.56 mmol) in methylene chloride (8 ml). The mixture was stirred for 2 hours at ambient temperature and poured onto a column of silica and eluted with increasingly polar mixtures of methylene chloride and ethyl acetate followed by ethyl acetate to give 4-chloro-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline (0.341 g, 78%).

Workup

  1. custom(prepared
  2. additionpoured onto a column of silica
  3. washeluted
  4. temperaturewith increasingly polar mixtures of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-3f2fd84057e14176918d5a20c6464a86
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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