Triphenylphosphine → HCID 18753449, compound

HRID 547209Notes

Reaction equation

HRID 547209 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Br:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([OH:31])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:54][NH:55][CH2:56][CH2:57][CH2:58]O>C(Cl)Cl>[Br:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH2:58][CH2:57][CH2:56][NH:55][CH3:54])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 101489863-(Methylamino)-1-propanolHCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

Product 1

HCID 18753449HCID 18753449, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (522 mg, 3 mmol) was added dropwise to a suspension of 4-(4-bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (364 mg, 1 mmol), (prepared as described for the starting material in Example 48), triphenylphosphine (786 mg, 3 mmol) and 3-methylamino-1-propanol (178 mg, 2 mmol), (J.Am.Chem.Soc., 1954, 76, 2789), in methylene chloride (4 ml) under nitrogen. The mixture was stirred for 1 hour at ambient temperature, neutral alumina (˜20 g) was added to the reaction mixture and the solvent was removed by evaporation. The powder was poured onto a column of neutral alumina and was eluted with a mixture of methylene chloride/methanol (95/5 followed by 90/10 and 80/20). The purified product was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-methylaminopropoxy)quinazoline (220 mg, 50%).

Workup

  1. custom(prepared
  2. additionneutral alumina (˜20 g) was added to the reaction mixture
  3. customthe solvent was removed by evaporation
  4. additionThe powder was poured onto a column of neutral alumina
  5. washwas eluted with a mixture of methylene chloride/methanol (95/5 followed by 90/10 and 80/20)
  6. customThe purified product was triturated with ether
  7. filtrationcollected by filtration
  8. washwashed with ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-dc72f018b41643edaa411f585769fe69
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

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