Carbonate Ion → 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine

HRID 1911372Notes

Reaction equation

HRID 1911372 reaction equation
C(=O)([O-])[O-].Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH2:23])[NH:21][N:22]=2)[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1>CO.O>[CH3:15][O:14][C:12]1[CH:11]=[C:10]([CH2:16][O:17][C:18]2[CH:19]=[C:20]([NH2:23])[NH:21][N:22]=2)[CH:9]=[C:8]([O:7][CH3:6])[CH:13]=1

Participants

5

Reactant 2

HCID 19660Carbonate IonHCID 574403805-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine hydrochloride

Product 1

HCID 574403815-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amineYield 67.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-[(3,5-Dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine was prepared as follows: MP carbonate (2.74 mmol/g) (12.00 g, 32.88 mmol) was added to 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine hydrochloride (5 g, 17.50 mmol) in methanol (200 mL) and water (20 mL). The resulting suspension was stirred at room temperature for 18 h. The reaction mixture was filtered and MP carbonate was washed with 10% MeOH in DCM. This was evaporated to dryness to afford 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine (2.94 g, 67.5%) as an orange waxy solid. 1H NMR (399.9 MHz, DMSO-d6) δ 3.74 (6H, s), 4.76 (1H, s), 4.97 (2H, s), 6.42 (1H, t), 6.55 (2H, d).

Workup

  1. custom5-[(3,5-Dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine was prepared
  2. filtrationThe reaction mixture was filtered
  3. washMP carbonate was washed with 10% MeOH in DCM
  4. customThis was evaporated to dryness

Sources & evidence

ORD record
ord-9df146c3a5e34ea7a1e3b0a1181fec57
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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