Triphenylphosphine → 7-(3-(4-Acetylpiperazin-1-yl)propoxy)-4-chloro-6-methoxyquinazoline

HRID 916394Notes

Reaction equation

HRID 916394 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.[C:46]([N:49]1[CH2:54][CH2:53][N:52]([CH2:55][CH2:56][CH2:57]O)[CH2:51][CH2:50]1)(=[O:48])[CH3:47]>>[C:46]([N:49]1[CH2:54][CH2:53][N:52]([CH2:55][CH2:56][CH2:57][O:26][C:20]2[CH:19]=[C:18]3[C:23]([C:14]([Cl:13])=[N:15][CH:16]=[N:17]3)=[CH:22][C:21]=2[O:24][CH3:25])[CH2:51][CH2:50]1)(=[O:48])[CH3:47]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 589602297-(3-(4-Acetylpiperazin-1-yl)propoxy)-4-chloro-6-methoxyquinazolineYield 66%

Procedure

Diethyl azodicarboxylate (0.243 g, 1.396 mmol) was added dropwise to a solution of 4-chloro-7-hydroxy-6-methoxyquinazoline (0.245 g, 1.16 mmol), triphenylphosphine (0.396 g, 1.51 mmol) and 3-(4-acetylpiperazin-1-yl)propan-1-ol (0.238 g, 1.28 mmol), (prepared as described for the starting material in Example 1 or Example 7). After stirring at ambient temperature for 1 hour, the mixture was poured onto silica and eluted with increasingly polar mixtures of methylene chloride and methanol to give 7-(3-(4-acetylpiperazin-1-yl)propoxy)-4-chloro-6-methoxyquinazoline (0.29 g, 66%).

Workup

  1. custom(prepared
  2. additionthe mixture was poured onto silica
  3. washeluted
  4. temperaturewith increasingly polar mixtures of methylene chloride and methanol

Sources & evidence

ORD record
ord-9357900f0bb84db68df6b17a76ba85e4
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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