Lithium Hydroxide → HCID 58548282, compound

HRID 2368220Notes

Reaction equation

HRID 2368220 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[N:16][CH:17]=2)=[N:9][CH:8]=[C:7]([CH:18]2[CH2:20][CH2:19]2)[N:6]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO>[CH:18]1([C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]([NH:11][C:12]3[CH:13]=[N:14][CH:15]=[N:16][CH:17]=3)=[N:9][CH:8]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58368051HCID 58368051, compound

Product 1

HCID 58548282HCID 58548282, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyrazine-2-carboxylic acid methyl ester (150 mg, 550 μmol) in THF (9 ml) and MeOH (1.8 ml) was cooled at 0° C. and treated with LiOH (1.66 ml, 1N aqueous solution). The ice bath was removed after 10 min and the reaction mixture was stirred at ambient temperature for 2 hrs. The reaction mixture was acidified with HCl (1.66 ml, 1N aqueous solution), diluted with water and extracted with dichloromethane. The combined organic layers were dried and concentrated in vacuo to yield a yellow solid. The aqueous phase was also concentrated in vacuo and the residue was triturated with ethyl acetate and sucked off to yield identical yellow solid (according to analytics). The solid material was combined to yield the product (75 mg, 52%)

Workup

  1. customThe ice bath was removed after 10 min
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. customThe combined organic layers were dried
  5. concentrationconcentrated in vacuo
  6. customto yield a yellow solid
  7. concentrationThe aqueous phase was also concentrated in vacuo
  8. customthe residue was triturated with ethyl acetate
  9. customto yield identical yellow solid (according to analytics)

Sources & evidence

ORD record
ord-abb8a10ea0344faab6785b277490eed6
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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