Sodium Hydroxide → 1-[4-amino-5-bromo-6-(prop-2-ynylamino)pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid

HRID 63610Notes

Reaction equation

HRID 63610 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[C:6]([NH:9][CH2:10][C:11]#[CH:12])[N:5]=[C:4]([N:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[CH:15]=[N:14]2)[N:3]=1.NC1C(Br)=C(Cl)N=C(N2C=C(C(OCC)=O)C=N2)N=1.C(N)C#C.[OH-].[Na+]>>[NH2:1][C:2]1[C:7]([Br:8])=[C:6]([NH:9][CH2:10][C:11]#[CH:12])[N:5]=[C:4]([N:13]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[N:14]2)[N:3]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 239041PropargylamineHCID 90303699HCID 90303699, compound2×HCID 90303792HCID 90303792, compound

Product 1

HCID 771075011-[4-amino-5-bromo-6-(prop-2-ynylamino)pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid

Procedure

The ethyl 1-[4-amino-5-bromo-6-(prop-2-ynylamino)pyrimidin-2-yl]-1H-pyrazole-4-carboxylate was obtained using the procedure described for example 1, but starting from ethyl 1-(4-amino-5-bromo-6-chloropyrimidin-2-yl)-1H-pyrazole-4-carboxylate (intermediate 18) and propargylamine. The ester was hydrolyzed with 1 M sodium hydroxide (10 eq.). The resulting sodium salt solution was extracted three times with 10 ml of DCM to remove organic impurities. The aqueous phase was acidified with 4 M HCl, the precipitate was filtered, washed several times with cold water and dried.

Workup

  1. extractionThe resulting sodium salt solution was extracted three times with 10 ml of DCM
  2. customto remove organic impurities
  3. filtrationthe precipitate was filtered
  4. washwashed several times with cold water
  5. customdried

Sources & evidence

ORD record
ord-74821872858e406e975090c4d09a9cfe
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Reaction notes

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