Isopropanol → 6-Chloro-2-fluoro-9-isopropyl-9H-purine

HRID 1241336Notes

Reaction equation

HRID 1241336 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[CH3:12][CH:13](O)[CH3:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:1][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:13]([CH3:14])[CH3:12]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178506011HCID 178506011, compound

Product 1

HCID 112873616-Chloro-2-fluoro-9-isopropyl-9H-purineYield 64%

Procedure

6-Chloro-2-fluoro-9H-purine (517.7 mg, 3 mmol), 2-propanol (198.3 mg, 3.3 mmol), PPh3 (866 mg, 3.3 mmol) was mixed under N2 in a 50 mL round-bottom flask at 0° C. DEAD (575 mg, 3.3 mmol) was added via syringe dropwise to the mixture. The temperature was raised to r. t. and the mixture was stirred overnight. Sovent was removed in vacuo and the resulting residue was chromatographed on silica gel (CH2Cl2/EtOAc, 4:1, Rf 0.62). The product was obtained as a white solid (411 mg, 64%).

Workup

  1. temperatureThe temperature was raised
  2. customSovent was removed in vacuo
  3. customthe resulting residue was chromatographed on silica gel (CH2Cl2/EtOAc, 4:1, Rf 0.62)

Sources & evidence

ORD record
ord-9d24d917877c4f3eaa465a6517f8dbd9
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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