3-Chloroaniline → (3-Chlorophenyl)-(2-fluoro-9-isopropyl-9H-purin-6-yl)amine

HRID 1241337Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].CCN(C(C)C)C(C)C>CCCCO>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:10]=[C:9]([F:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]([CH3:14])[CH3:13])[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 90 °C

Procedure

6-Chloro-2-fluoro-9-isopropyl-9H-purine (214 mg, 1 mmol) was mixed with 3-chloroaniline (127.6 mg, 1 mmol) in 12 mL n-BuOH. DIEA (357.6 mg, 2.8 mmol) was added and the solution was heated at 90° C. overnight. Solvent was removed in vacuo and the residue was chromatographed on silica gel (CH2Cl2/EtOAc 2:2, Rf 0.44) to get the product as a white solid (148 mg, 48%).

Workup

customSolvent was removed in vacuo
customthe residue was chromatographed on silica gel (CH2Cl2/EtOAc 2:2, Rf 0.44)

Sources & evidence

ORD record: ord-56d88a99118a4df790fc467b97294f7d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115589B2

Reaction notes

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