Diisopropylethylamine → HCID 66635662, compound

HRID 872112Notes

Reaction equation

HRID 872112 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:5]2[N:15]=[C:16]([CH3:19])[C:17]([I:18])=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.[NH:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][OH:35]>C(#N)C>[CH3:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]3[N:15]=[C:16]([CH3:19])[C:17]([I:18])=[C:4]3[N:3]=[C:2]([N:29]3[CH2:33][CH2:32][CH2:31][C@H:30]3[CH2:34][OH:35])[CH:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 86688012HCID 86688012, compound

Product 1

HCID 66635662HCID 66635662, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-7-(3-methylphenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine (580 mg), DIPEA (0.4 mL) and (S)-2-pyrrolidinemethanol (400 mg) are stirred at 90° C. in an acetonitrile (60 mL) solvent for 6 hours. The reaction solvent is removed by distillation under reduced pressure. The remainder is purified by column chromatography to yield the target compound (360 mg). 1H NMR (CDCl3, 300 MHz): δ 7.67 (m, 2H), 7.40 (m, 2H), 7.27 (s, 1H), 6.10 (s, 1H), 4.48 (br, 1H), 3.88-3.55 (m, 4H), 2.44 (s, 3H), 2.38 (s, 3H), 2.08-1.97 (m, 3H), 1.76 (m, 1H).

Workup

  1. customThe reaction solvent is removed by distillation under reduced pressure
  2. customThe remainder is purified by column chromatography

Sources & evidence

ORD record
ord-9b1d30be90844424bdb9fdf1984743fe
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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