Ethanol → 2-(2-Chlorophenyl)-7-ethoxy-3-iodopyrazolo[1,5-a]pyrimidine

HRID 348022Notes

Reaction equation

HRID 348022 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10]([I:11])=[C:6]2[N:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21]([OH:23])[CH3:22]>>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[C:10]([I:11])=[C:6]2[N:5]=[CH:4][CH:3]=[C:2]([O:23][CH2:21][CH3:22])[N:7]2[N:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 21083717HCID 21083717, compound

Product 1

HCID 210837012-(2-Chlorophenyl)-7-ethoxy-3-iodopyrazolo[1,5-a]pyrimidine

Procedure

To a mixture of 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 6.80 g, 17.4 mmol) in ethanol (175 ml) was added NaH (60% dispersion in oil, 439 mg, 18 mmol), portionwise. After stirring overnight, the suspended solids were isolated by vacuum filtration to afford, after drying, in vacuo, product I-11A-1a (6.87 g, 99%) as a solid: +APcI MS (M+1) 400.0; 1H NMR (400 MHz, CD3OD) δ 8.51 (d, J=5.0 Hz, 1H), 7.58–7.40 (m, 4H), 6.67 (d, J=5.0 Hz, 1H), 4.58 (q, J=7.1 Hz, 2H), 1.58 (t, J=7.1 Hz, 3H).

Workup

  1. customthe suspended solids were isolated by vacuum filtration
  2. customto afford
  3. customafter drying, in vacuo, product I-11A-1a (6.87 g, 99%) as a solid

Sources & evidence

ORD record
ord-d4cfcf2427e244e8ac717950df766772
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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