6-Chloro-2-fluoropurine

Beige solid

6-Chloro-2-fluoro-9H-purine: 6-CHLORO-2-FLUORO-9H-PURINE] This compound was prepared by a modification of a literature procedures (Gray, N. S.; Kwon, [S. ;] Schultz, P. G. Tetrahedron Lett. 1997, 38 (7), 1161-1164.) [6-CHLORO-9H-PURIN-2-YLAMINE] (75.0 g, 0.44 mol) was suspended in aq HBF4 (1.5 L of 48 percent w/w solution in H2O). This mixture was cooled to-15 [°C] and was stirred vigorously. NaNO2 (2.5 L of an 0.3 M aq solution) was then added slowly over 75 min with stirring and careful temperature control (< 10 [°C).] After complete addition, the pale yellow solution was further stirred at room temperature for 30 min. It was then re- cooled to-15 [°C] and was neutralised carefully to pH = 6.2 with [NAOH] (50 percent w/v aq solution). This solution was rotary evaporated to semi-dryness. The resulting cake was divided with a spatula and dried under high vacuum overnight. The resulting yellow powder was dry-loaded onto a flash chromatography column (24 x 15 cm [SI02] bed), which was eluted with [CH2CL2/MEOH, ] 9: 1. Appropriate fractions were collected, pooled, and evaporated. After drying in vacuo, the title compound (34.8 g, 48 percent) was obtained as a colourless powder. TLC: [RF=] 0.25 [(CH2CL2/MEOH, ] 9: 1), starting material Rf= 0.16. m/z 173 (MH+, 100), 175 [(MH+2, ] 33)This compound was prepared by a modification of a literature procedures (Gray, N. S.; Kwon, S.; Schultz, P. G. Tetrahedron Lett. 1997, 38 (7), 1161-1164.) [CHLORO-9H-PURIN-2-YLAMINE] (75.0 g, 0.44 mol) was suspended in aq HBF4 (1.5 L of 48 percent w/w solution in H2O). This mixture was cooled to-15 C and was stirred vigorously. NaN02 (2.5 L of an 0.3 M aq solution) was then added slowly over 75 min with stirring and careful temperature control (< 10 C). After complete addition, the pale yellow solution was further stirred at room temperature for 30 min. It was then re-cooled to- 15 [C] and was neutralised carefully to pH = 6.2 with [NAOH] (50 percent w/v aq solution). This solution was rotary evaporated to semi-dryness. The resulting cake was divided with a spatula and dried under high vacuum overnight. The resulting yellow powder was dry-loaded onto a flash chromatography column (24 x 15 cm Si02 bed), which was eluted with CH2Cl2/MeOH, 9: 1. Appropriate fractions were collected, pooled, and evaporated. After drying in vacuo, the title compound (34.8 g, 48 percent) was obtained as a colourless powder. TLC: Rf = 0.25 (CH2Cl2/MeOH, 9: 1), starting material Rf = [0.] [16.] m/z 173 (MH+, 100), 175 [(MH+2, ] 33).

Used as pharmaceutical intermediate

Molecular Weight:172.55
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:171.9952019
Monoisotopic Mass:171.9952019
Topological Polar Surface Area:54.5
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes