HCID 59784645, compound → HCID 59785015, compound

HRID 470319Notes

Reaction equation

HRID 470319 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH2:26])=[N:8][N:9]([C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:10]=1)=[O:5])C>[OH-].[K+].CO>[NH2:26][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][N:9]([C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[CH:14]=[CH:13][N:12]=2)[N:8]=1

Participants

4

Reactant 1

HCID 59784645HCID 59784645, compound

Product 1

HCID 59785015HCID 59785015, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 3-Amino-1-[4-(4-dimethylamino-phenyl)-pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (250 mg, 0.71 mM) in 1 N KOH (3 ml) and MeOH (4 ml) was heated at 95° C. for 1 hr allowing some methanol to distil off. The reaction was cooled to room temperature and neutralized with 1 N HCl. The resulting precipitate was collected via filtration, washed with water (1×3 ml) and then dried in vacuo overnight to afford 3-Amino-1-[4-(4-dimethylamino-phenyl)-pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid (170 mg, 73% yield) as a yellow solid. ES-MS MH+325.4 1H NMR (300 MHz, ppm, DMSO-d6): 8.72 (s, 1H), 8.60 (d, 1H), 8.15 (d, 2H), 7.70 (d, 1H), 6.82 (d, 2H), 5.77 (br, 2H), 3.03 (s, 6H)

Workup

  1. customto distil off
  2. temperatureThe reaction was cooled to room temperature and neutralized with 1 N HCl
  3. filtrationThe resulting precipitate was collected via filtration
  4. washwashed with water (1×3 ml)
  5. customdried in vacuo overnight

Sources & evidence

ORD record
ord-ece18b268c074df4b1e70c8d75862be8
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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