Lithium Hydroxide → HCID 70099899, compound

HRID 2368338Notes

Reaction equation

HRID 2368338 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:30])[S:9][C:10]=1[NH:11][C:12]([C:14]1[C:19]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[N:25][CH:26]=2)=[N:18][CH:17]=[C:16]([CH:27]2[CH2:29][CH2:28]2)[N:15]=1)=[O:13])=[O:5])C.[OH-].[Li+]>C1COCC1.C(O)C>[CH:27]1([C:16]2[N:15]=[C:14]([C:12]([NH:11][C:10]3[S:9][C:8]([CH3:30])=[N:7][C:6]=3[C:4]([OH:5])=[O:3])=[O:13])[C:19]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[N:23][CH:22]=3)=[N:18][CH:17]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70098737HCID 70098737, compound

Product 1

HCID 70099899HCID 70099899, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carbonyl]-amino}-2-methyl-thiazole-4-carboxylic acid ethyl ester (70 mg, 0.16 mmol) in a THF/ethanol mixture (2.5 ml; 1.5:1) was cooled to 0° C. and treated with lithium hydroxide (0.82 ml; 1N aqueous solution). After 15 min, the cooling bath was removed and the reaction mixture was stirred at 50° C. overnight. The reaction mixture was cooled to r.t. and 0.84 ml 1M HCl was added. The suspension was filtered, the solid was washed with water and THF and dried in vacuo to yield 28 mg (43%) of a yellow solid.

Workup

  1. customthe cooling bath was removed
  2. temperatureThe reaction mixture was cooled to r.t.
  3. addition0.84 ml 1M HCl was added
  4. filtrationThe suspension was filtered
  5. washthe solid was washed with water and THF
  6. customdried in vacuo

Sources & evidence

ORD record
ord-323919314ca444b593e704743365f3f6
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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