Diisopropylethylamine → (S)-(1-(7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol

HRID 872089Notes

Reaction equation

HRID 872089 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[N:5]2[N:16]=[C:17]([CH3:20])[C:18]([I:19])=[C:4]2[N:3]=1.CCN(C(C)C)C(C)C.[NH:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH2:35][OH:36]>C(#N)C>[F:15][C:10]1[CH:9]=[C:8]([C:6]2[N:5]3[N:16]=[C:17]([CH3:20])[C:18]([I:19])=[C:4]3[N:3]=[C:2]([N:30]3[CH2:34][CH2:33][CH2:32][C@H:31]3[CH2:35][OH:36])[CH:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 866880045-Chloro-7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 68026319(S)-(1-(7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloro-7-(3,4-difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine (401 mg), DIPEA (0.35 mL) and (S)-2-pyrrolidinemethanol (401 mg) are stirred for 2.5 hours in an acetonitrile (60 mL) solvent at 90° C. The reaction solvent is removed by distillation under reduced pressure. The remainder is purified by column chromatography to yield the target compound (395 mg). 1H NMR (CDCl3, 300 MHz) δ 7.82 (m, 1H), 7.67 (m, 1H), 7.29 (q, J=8.7 Hz, 1H), 6.11 (s, 1H), 4.45 (br, 1H), 3.85 (m, 1H), 3.77 (m, 1H), 3.57 (m, 2H), 2.38 (s, 3H), 2.08-2.01 (m, 3H), 1.70 (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-ed050cef4d5c414fbf3498207512e27b
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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