Acetic Acid → 2-bromo-5-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

HRID 62221Notes

Reaction equation

HRID 62221 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH:8]=[C:9](O)[C:10]([F:13])([F:12])[F:11])[C:4]([CH3:16])=[N:3]1.[Br:17][C:18]1[CH:22]=[C:21]([NH2:23])[NH:20][N:19]=1.[C:24](O)(=O)C>>[Br:17][C:18]1[CH:22]=[C:21]2[N:23]=[C:7]([C:5]3[C:4]([CH3:16])=[N:3][N:2]([CH2:1][CH3:24])[CH:6]=3)[CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[N:20]2[N:19]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 178434003HCID 178434003, compoundHCID 178507227HCID 178507227, compound

Product 1

HCID 867041792-bromo-5-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidineYield 73.1%

Procedure

1-(1,3-dimethyl-1H-pyrazol-4-yl)-4,4,4-trifluoro-3-hydroxybut-2-en-1-one (Preparation 5, 1.7 g) and 3-bromo-1H-pyrazol-5-amine (Preparation 6, 1.18 g) in Acetic acid (52.61 mL) was heated at 120° C. in a sealed tube overnight. The reaction solution was cooled to room temperature, and poured into ice water (500 mL) resulting in a white precipitate. The precipitate was filtered and washed with copious amounts of water. The precipitate was then collected and dried in vacuo to afford the title compound as a white powder (1.9 g, 73.1%). 1H NMR (400 MHz, DMSO-d6) δ: 2.47 (s, 3H), 3.79, (s, 3H), 6.95, (s, 1H), 7.73, (s, 1H), 8.67, (s, 1H).

Workup

  1. customresulting in a white precipitate
  2. filtrationThe precipitate was filtered
  3. washwashed with copious amounts of water
  4. customThe precipitate was then collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-07e0eeac0a1c420691f9f9ce76905fa7
Source dataset
uspto-grants-2016_09
Patent number
US09446046B2

Reaction notes

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