p-Toluenesulfonic acid → HCID 178478372, compound

HRID 334122Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7](C2CCCCO2)[C:8]2[C:13]([N:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:11]=[C:10]([Cl:21])[N:9]=2.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[NH:7][C:8]2[C:13]([N:14]=1)=[C:12]([N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[N:11]=[C:10]([Cl:21])[N:9]=2

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 4-(8-(4-bromobutyl)-2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholine (1.1 g, 2.4 mmol) in methanol (10 mL) was treated with p-toluenesulfonic acid (40 mg, 0.24 mmol) and heated overnight at 50° C. The solvent was removed in vacuo to afford 4-(8-(4-bromobutyl)-2-chloro-9H-purin-6-yl)morpholine as a white solid, which was used in the next step without any further purification (880 mg, quant). LC/MS (ESI+): m/z 375 (M+H)

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-8fc0249c336d47c7874fa67d56f27ff6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883799B2

Reaction notes

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