Xyloand Arabinosuranosylthioguaninb of 6-chloro-2-fluoropurine (I, 1.5 g, 8.6 mmoles) in 25% methanolic Me3N was kept at 25°. After a few min a cryst ppt appeared. The mixt was kept at 25°for 48 hr; the ppt was collected and washed with EtOH to yield colorless plates (0.45 g, 26%), mp 300°, of 2-fluoro-6-trimethylaminopurine betaine (XX): uvmax (pH 1.0) 270.5 (c 7.9 X 103), (pH 6) 273 (7.3 X 103), (pH 12) 273 nm (7.6 X 103). Anal. (CSHUN5F) C, , N, F.The filtrate of the above reaction, after evapn to dryness under reduced pressure, gave a cryst residue consisting of 2-fiuoro-6dimethylaminopurine (XIX), 1.1 g (70%), mp 220°. Anal.(CvHgNsF) C, , N, F. This material was identical with the product prepared by Montgomery and Hewson.6 Reaction of 2-Fluoro-6-chloropurine (I) with Hydrazine.-A 10% hydrazine hydrate ethanolic soln (25 ml) was added to 2-fluoro-6-chloropurine (I, 1.5 g, 8.7 mmoles) dissolved in EtOH (25 ml) at 5°. After stirring at 5°for 1 hr, the resulting ppt was collected by filtration, and dried to yield 2-fluoro-6-hydrazinopurine (XXI), 1.3 g (87%) of thin needles, mp 142°. Anal. (C5HcN6F) C, , N, F.When XXI (20 mg) was boiled in H20 (5 ml) and Raney Ni (50 mg) for 2 hr, the resulting soln showed uv spectra and Ri values identical with those of 2-fluoroadenine (VIII).6,6-Bis(2-fluoroadenine) (XXII).-Solus of 2-fluoro-6-chloropurine (I, 1.20 g, 6.9 mmoles) in EtOH (25 ml) and 2-fluoro-6hydrazinopurine (XXI, 1.15 g, 6.9 mmoles) in 70% aq EtOH (25 ml) were combined. Anhyd NaOAc (0.67 g, 7.6 mmoles) was added, and the mixt was refluxed for 6 hr and kept at 25°o vernight. The ppt which formed was collected by filtration and repeatedly washed with H20 and EtOH to yield 1.03 g (quant) of a yellow microcryst product, mp >300°. Anal. (Ci0H6NioF2) C, , N. F test was positive.Treatment of XXII with Raney Ni.-A suspension of XXII (0.5 g, 1.6 mmoles) in H20 (25 ml) and Raney Ni (3 g) was refluxed for 12 hr. The reaction mix was filtered when hot, the Ni was washed with boiling H20, and the combined filtrates were evapd to dryness under reduced pressure. The residue was suspended in H20 (5 ml), filtered, and dried to yield 70 mg (14%) of 2-fluoroadenine (VIII).2-Hydroxylamino-6-aminopurine (2-Hydroxylaminoadenine) (XXIII).-A suspension of VIII (0.30 g, 1.8 mmoles) in 0.6 M ethanolic HONH2 (300 ml) and 0.3 ml of 30% aq soln of HONH2• HC122 was refluxed for 6 hr and kept at 25°o vernight. The (22) A