Hydrochloric Acid → HCID 68701198, compound

HRID 220090Notes

Reaction equation

HRID 220090 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[N:15]=[CH:14][N:13]=2)[C:10]=1[NH2:11])=[O:5])C.[OH-].[Li+].Cl>O1CCOCC1.O>[NH2:11][C:10]1[N:9]([C:12]2[CH:17]=[C:16]([N:18]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH3:19])[N:15]=[CH:14][N:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59173386HCID 59173386, compound

Product 1

HCID 68701198HCID 68701198, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-amino-1-[6-(tert-butoxycarbonyl-methyl-amino)-pyrimidin-4-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (5.5 g, 15.2 mmol), lithium hydroxide (1.82 g, 75.8 mmol) dissolved in a mixture of 1,4-Dioxane (20 mL) and water (5 mL) is heated to 85° C. for 8 hours. The reaction mixture is then neutralized with 2 M HCl aqueous solution until pH˜4-5 causing a white precipitate to form. After filtration, the undissolved solid is washed with small amount of water, air-dried to give 5-amino-1-[6-(tert-butoxycarbonyl-methyl-amino)-pyrimidin-4-yl]-1H-pyrazole-4-carboxylic acid as white powder: 1H NMR 400 MHz (d6-DMSO) δ 8.41 (s, 1H), 8.00-7.40 (m, 4H), 6.86-6.58 (m, 1H), 2.86 (s, 3H); MS m/z 235.10 (M+1).

Workup

  1. customto form
  2. filtrationAfter filtration
  3. washthe undissolved solid is washed with small amount of water
  4. customair-dried

Sources & evidence

ORD record
ord-8811e6dec7ae4167849876b1d7fa24da
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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