(+)-Glycidol → HCID 69779981, compound

HRID 897641Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3=[N:10][CH:11]=[N:12][C:13]([NH2:14])=[C:8]3[C:7]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)=[N:6]2)[CH2:2]1.[CH2:28]1[O:30][C@@H:29]1[CH2:31][OH:32]>>[NH2:14][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[N:5]([CH:3]3[CH2:2][N:1]([CH2:28][C@H:29]([OH:30])[CH2:31][OH:32])[CH2:4]3)[N:6]=[C:7]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[C:8]=12

Participants

Reactant 2

HCID 5460455(+)-Glycidol

HCID 223471371-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 69779981HCID 69779981, compoundYield 37.9%

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.05 g, 0.00014 mol) was added (R)-(+)-glycidol (0.05 M in isopropanol, 2.8 mL, 0.00014 mol) at room temperature under an atmosphere of nitrogen. The mixture was stirred at 80° C. for three hours. The solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using ammonium hydroxide/methanol/dichloromethane (2:7:91) followed by ammonium hydroxide/methanol/dichloromethane (2:10:88) as mobile phase to yield (2S)-3-{3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanyl}propane-1,2-diol (0.023 g, 0.000053 mol).

Workup

customThe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-a9025b5fbe464e6095349575eb8484c4
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Reaction notes

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