Hydrochloric Acid → 6-Ethynyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 657698Notes

Reaction equation

HRID 657698 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[C:9][Si](C)(C)C)=[C:6]([NH2:14])[N:5]2[N:15]=[CH:16][N:17]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O1CCCC1.O>[C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]2[N:5]([N:15]=[CH:16][N:17]=2)[C:6]=1[NH2:14])#[CH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 667431075-Methyl-6-((trimethylsilyl)ethynyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 871324066-Ethynyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amineYield 40.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of Example 72A (122 mg, 0.5 mmol), potassium carbonate (138 mg, 1.0 mmol) in a mixed solvent of methanol/tetrahydrofuran/H2O(3 mL/3 mL/0.5 mL) was stirred at room temperature for 1.5 h. The reaction mixture was acidified with 1N HCl. The solid was filtered, washed with water and ethyl acetate to provide the title compound as an off-white solid (35 mg, 40% yield).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-a647cc33e857455c9159cda5f8fb8ce0
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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