Sodium Hydroxide → 2-(5-Bromo-2-(methylthio)pyrimidin-4-yl)thiazolo[5,4-c]pyridine

HRID 2267319Notes

Reaction equation

HRID 2267319 reaction equation
C(N(CC)C([S:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13][C:14]([C:16]1[N:21]=[C:20]([S:22][CH3:23])[N:19]=[CH:18][C:17]=1[Br:24])=O)=S)C.[OH-].[Na+]>C(O)=O>[Br:24][C:17]1[C:16]([C:14]2[S:6][C:7]3[CH:8]=[N:9][CH:10]=[CH:11][C:12]=3[N:13]=2)=[N:21][C:20]([S:22][CH3:23])=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 602043714-(5-Bromo-2-(methylthio)pyrimidine-6-carboxamido)pyridin-3-yl diethylcarbamodithioate

Product 1

HCID 574288282-(5-Bromo-2-(methylthio)pyrimidin-4-yl)thiazolo[5,4-c]pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A stirred solution of 4-(5-bromo-2-(methylthio)pyrimidine-6-carboxamido)pyridin-3-yl diethylcarbamodithioate (1.99 g, 4.21 mmol) in 96% formic acid (40 mL) was heated to reflux for 4 h. After cooling to r.t. the reaction mixture was poured into ice/water (400 mL), then basified with 5 N aqueous sodium hydroxide and extracted with ethyl acetate (3×150 mL). The organic layers were combined, dried over sodium sulfate, filtered and the solvent evaporated in vacuo to yield 2-(5-bromo-2-(methylthio)pyrimidin-4-yl)thiazolo[5,4-c]pyridine (1.34 g, 94%) as a yellow amorphous solid. 1H NMR: δ (CDCl3, 400 MHz) 2.67 (s, 3 H), 8.09 (d, J=5.5 Hz, 1 H), 8.74 (d, J=5.5 Hz, 1 H), 8.86 (s, 1 H), 9.34 (s, 1 H).

Workup

  1. temperatureto reflux for 4 h
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-01fc4201c7a545fbb8bb4fd868dfc934
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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