TFA dichloromethane water → 2-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acid

HRID 643736Notes

Reaction equation

HRID 643736 reaction equation
C([O:5][C:6]([C:8]1[S:24][C:11]2=[CH:12][CH:13]=[C:14]3[C:19]([N:18]=[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])[N:16]=[CH:15]3)=[C:10]2[CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.O>>[CH3:23][S:20]([C:17]1[N:16]=[CH:15][C:14]2[C:19](=[C:10]3[CH:9]=[C:8]([C:6]([OH:7])=[O:5])[S:24][C:11]3=[CH:12][CH:13]=2)[N:18]=1)(=[O:21])=[O:22]

Participants

3

Reactant 2

HCID 18672661TFA dichloromethane waterHCID 592629202-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl ester

Product 1

HCID 592628242-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acidYield 99%

Procedure

2-Methanesulfonyl-thieno[2,3-h]quinazoline-8-carboxylic acid tert-butyl ester (4.20 g, 11.52 mmol) was placed in a 500 mL Florentine and cooled in an ice-bath. Pre-mixed TFA:DCM:water (1:1:0.025, 4.5 mL) was added in one portion and the resultant solution was stirred at 0° C. for 0.75 hours and a further 0.75 hours at room temperature. The reaction mixture was concentrated under reduced pressure and azeotroped with portions of DCM (5×50 mL) and Et2O (5×50 mL). The solid obtained was triturated with Et2O, filtered and washed with Et2O (3×5mL) to give a light yellow powder (3.51 g, 99% yield). δH (d6 DMSO) 3.6-3.7(3H, s), 8.3(1H, d), 8.6(1H, d), 8.8(1H, s), 9.9-10.0(1H, s), 13.8-14.0(1H, br s)

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customazeotroped with portions of DCM (5×50 mL) and Et2O (5×50 mL)
  4. customThe solid obtained
  5. customwas triturated with Et2O
  6. filtrationfiltered
  7. washwashed with Et2O (3×5mL)

Sources & evidence

ORD record
ord-9d9b425d372040cd9fd354124f1de96c
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Reaction notes

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