2-Methyl-2-thiopseudourea → 4-{5-Chloro-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl methyl ether

HRID 1796560Notes

Reaction equation

HRID 1796560 reaction equation
[CH3:1][S:2][C:3](=[NH:5])[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:18]=[CH:17][N:16]2[N:19]=[C:20]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:21]([C:22](=O)[C:23]#[CH:24])=[C:15]2[CH:14]=1.C(OCC)(=O)C>C(O)C>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:20]2[C:21]([C:22]3[CH:23]=[CH:24][N:4]=[C:3]([S:2][CH3:1])[N:5]=3)=[C:15]3[CH:14]=[C:13]([Cl:12])[CH:18]=[CH:17][N:16]3[N:19]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 51422-Methyl-2-thiopseudoureaHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 221809211-[5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one

Product 1

HCID 221809204-{5-Chloro-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl methyl etherYield 31.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of 2-methyl-2-thiopseudourea (358 mg, 1.29 mmol) and potassium carbonate (178 mg, 1.29 mmol) in ethanol was stirred at room temperature for 10 minutes. 1-[5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (200 mg, 0.64 mmol) was added. The suspension was stirred at room temperature for 12 hours. Ethyl acetate was added. The ethyl acetate phase was washed with water and brine and dried over magnesium sulfate. Filtration and concentration, followed by chrornatography (3:2 hexanes/ethyl acetate), gave 4-{5-chloro-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl methyl ether (77 mg, 31%) as a white solid. 1H NMR (CDCl3) δ 8.49 (d, 1H), 8.37 (d, 1H), 8.20 (d, 1H), 7.48 (d, 2H), 6.98 (d, 2H), 6.85 (dd, 1H), 6.70 (d, 1H), 3.85 (s, 3H), 2.62 (s, 3H). MS m/z 383 (M+1).

Workup

  1. stirringThe suspension was stirred at room temperature for 12 hours
  2. washThe ethyl acetate phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-88c011a12695402ea0bb040ef65ac4b2
Source dataset
uspto-grants-2006_04
Patent number
US07030134B2

Reaction notes

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