p-Toluenesulfonic acid → HCID 178450354, compound

HRID 334134Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17]([OH:21])([CH2:19][CH3:20])[CH3:18])[N:8]2C2CCCCO2)=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17]([OH:21])([CH2:19][CH3:20])[CH3:18])[NH:8]2)=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 2-(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)butan-2-ol (3.87 g, 9.8 mmol) in methanol (110 mL) was treated with p-toluenesulfonic acid (170 mg, 0.98 mmol) and heated overnight at 50° C. The solvent was removed in vacuo to afford 2-(2-chloro-6-morpholino-9H-purin-8-yl)butan-2-ol as a white solid, which was used in the next step without any further purification (3.0 g, quant). LC/MS (ESI+): m/z 312 (M+H)

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-f21d9a7ca78c4050a679b069a58e7758
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883799B2

Reaction notes

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