Bis(tributyltin) oxide → (4-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid

HRID 472730Notes

Reaction equation

HRID 472730 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:23][C:24](=[O:37])[NH:25][C:26]3[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:27]=3[O:35][CH3:36])[C:13]2=[O:38])=[CH:8][CH:7]=1)C.CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[Cl:32][C:30]1[C:29]([O:33][CH3:34])=[CH:28][C:27]([O:35][CH3:36])=[C:26]([NH:25][C:24]([CH2:23][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:22])[N:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:39])=[O:3])=[CH:7][CH:8]=3)[C:13]2=[O:38])=[O:37])[CH:31]=1

Participants

4

Reactant 2

HCID 16682746Bis(tributyltin) oxideHCID 68591686(4-[1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid ethyl ester2×

Product 1

HCID 59317701(4-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

(4-[1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid ethyl ester (Intermediate K) (105.4 mg, 0.19 mmol) is added to a stirred solution of Bis(tributyltin)oxide) (2 eq, 0.38 mmol, 193.1 μL) in toluene (10 ml). The mixture is heated at reflux at 120° C. for 72 hours. The toluene is removed in vacuo, and the red/brown oily residue is partitioned between EtOAc and saturated NaHCO3 (5 ml). The resultant precipitate is filtered, washed with NaHCO3, EtOAc, 1M HCl, water, and dried to give the title compound, [M+H]+ 524

Workup

  1. temperatureThe mixture is heated
  2. customThe toluene is removed in vacuo
  3. customthe red/brown oily residue is partitioned between EtOAc and saturated NaHCO3 (5 ml)
  4. filtrationThe resultant precipitate is filtered
  5. washwashed with NaHCO3, EtOAc, 1M HCl, water
  6. customdried

Sources & evidence

ORD record
ord-a545bf03cf0d4aaf9ba2e9d111ad579d
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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