Triphenylphosphine → HCID 21936093, compound

HRID 1241574Notes

Reaction equation

HRID 1241574 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:33])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[C:18]2[O:34][CH2:35][O:36][C:17]2=[CH:16][CH:15]=1.O[CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:13][C:14]1[C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH2:38][CH2:39][N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[C:18]2[O:34][CH2:35][O:36][C:17]2=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 135594114HCID 135594114, compound

Product 1

HCID 21936093HCID 21936093, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (0.182 ml) was added dropwise to a stirred mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-hydroxy-6-methoxyquinazoline (0.2 g), N-(2-hydroxyethyl)pyrrolidine (0.086 g), triphenylphosphine (0.303 g) and methylene chloride (3 ml) and the reaction mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using a 45:4:1 mixture of methylene chloride, methanol and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound (0.033 g) as a white solid; NMR Spectrum: (DMSOd6 and CF3CO2D) 1.9 (m, 2H), 2.1 (m, 2H), 3.2 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 4.05 (s, 3H), 4.6 (m, 2H),6.2 (s, 2H), 7.1 (d, 1H), 7.5 (s, 1H), 8.2 (s, 1H), 8.95 (s, 1H); Mass Spectrum: M−H− 441 and 443.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. additiona 45:4:1 mixture of methylene chloride, methanol

Sources & evidence

ORD record
ord-5d84eb2fe9b04c2dbbcea67c2db48ea4
Source dataset
uspto-grants-2006_10
Patent number
US07115615B2

Reaction notes

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