Triethylamine → 1-(4-(2-(2-Hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-(methylthio)butane-1,2-dione

HRID 2079321Notes

Reaction equation

HRID 2079321 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][S:26][CH2:27][CH2:28][C:29](=[O:33])[C:30]([O-])=[O:31].[Na+].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:8]1[N:7]=[C:6]([N:19]2[CH2:24][CH2:23][N:22]([C:30](=[O:31])[C:29](=[O:33])[CH2:28][CH2:27][S:26][CH3:25])[CH2:21][CH2:20]2)[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 23696623Sodium 4-(methylthio)-2-oxobutanoateHCID 1361346166-[7-methyl-4-(1-piperazinyl)-1H-quinazolin-2-ylidene]-1-cyclohexa-2,4-dienone

Product 1

HCID 1361213251-(4-(2-(2-Hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-(methylthio)butane-1,2-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(7-methyl-4-(piperazin-1-yl)quinazolin-2-yl)phenol (200 mg, 0.63 mmol), sodium 4-methylsulfanyl-2-oxo-butyrate (160 mg, 0.94 mmol), BOP (414 mg, 0.94 mmol), and triethylamine (348 μL, 2.5 mmol) in 2.1 mL of CH2Cl2 was stirred at room temperature for 1 h. After adding saturated NaHCO3 solution, the mixture was extracted with CH2Cl2. The organic extracts were dried over Na2SO4 and concentrated to give 1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-(methylthio)butane-1,2-dione. LC/MS: m/z 451.2 (M+H)+ at 3.10 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-afa1dab01f90461bbea21e82833d539d
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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