Sodium Hydroxide → 3-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid

HRID 1409998Notes

Reaction equation

HRID 1409998 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[C:13]3[N:18]=[CH:17][S:16][C:14]=3[N:15]=2)[CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([NH:19][C:12]2[C:13]3[N:18]=[CH:17][S:16][C:14]=3[N:15]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[N:11]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 683794533-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester

Product 1

HCID 665513433-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acidYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[7-(3,4-dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester (0.85 g, 2 mmol) in 20 mL of THF and 20 mL of methanol was added a solution of NaOH (0.08 g, 20 mmol) in 2 mL of water at room temperature. Then the reaction was stirred at this temperature for 16 hours. The solvent was evaporated and the residue was suspended in 50 mL of THF, then treated by 6N HCl until pH=3. The solvent was evaporated and then dissolved in 30 mL of THF, filtered. The filtrate was evaporated to give 3-[7-(3,4-dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid (0.8 g, 97.5%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 13.15 (s, 1H), 10.18 (s, 1H), 9.38 (s, 1H), 8.98 (s, 1H), 8.61 (d, 1H, J=8.1 Hz), 8.06 (d, 1H, J=7.5 Hz), 7.84 (d, 1H, J=2.4 Hz), 7.64 (t, 1H, J=7.8 Hz), 7.42 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.98 (d, 1H, J=8.7 Hz), 3.82 (s, 3H), 3.77 (s, 3H). LC-MS: 409 [M+H]+, 839 [2M+Na]+, tR=1.74 min. HPLC: 98.38% at 214 nm, 97.29% at 254 nm, tR=3.44 min.

Workup

  1. customThe solvent was evaporated
  2. additiontreated by 6N HCl until pH=3
  3. customThe solvent was evaporated
  4. dissolutiondissolved in 30 mL of THF
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-133ebc6092a340bb8edd591337de76c7
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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