(4-BROMOTHIAZOL-5-YL)METHANOL

To a solution of(2, 4-dibromothiazol-5-yl)methanol (15.0 g, 54.9 mmol) in methanol (400 mL)was added 10percent Pd/C (1.12 g) followed by Na2CO3 (13.0 g) at RT. The reaction mixture was hydrogenated at 60 psi for 2 days at room temperature. The reaction mixture was filtered, washed with ethyl acetate and concentrated. Purification of the evaporation residue by column chromatography (30percent EtOAc in petroleum ether) afforded 9.3 g of(4-bromothiazol-5 -yl)methanol as yellow liquid.To a stirred mixture of To a solution of Example 65a (426 mg, 2.2 mmol) in Dioxane (10 mL) and water (1 mL) was added Example lb (507 mg, 3.3 mmol) and Na2C03 (467 mg 4.4 mmol) Pd2(dba)3 (50 mg), X-phos (50 mg) under N2. The mixture was then heated to 105C for lhr. The residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 65b (270 mg, yield 55%) as yellow oil. LCMS [M+1]+=224.1Sodium hydride (1.67 g, 69.97 mmol, 60%) was washed with dry n-pentane and dried under vacuum. Dry THF (300 mL) was added and the mixture was cooled in ice/water bath. A solution ofTo a pale yellow solution of To a pale yellow solution of To a solution of(2, 4-dibromothiazol-5-yl)methanol (15.0 g, 54.9 mmol) in methanol (400 mL)was added 10% Pd/C (1.12 g) followed by Na2CO3 (13.0 g) at RT. The reaction mixture was hydrogenated at 60 psi for 2 days at room temperature. The reaction mixture was filtered, washed with ethyl acetate and concentrated. Purification of the evaporation residue by column chromatography (30% EtOAc in petroleum ether) afforded 9.3 g of(4-bromothiazol-5 -yl)methanol as yellow liquid.d) (4-Bromo-1, 3-thiazol-5-yl)methyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2, 3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate. Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2, 3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (28 mg, 0.061 mmol) was mixed with d (4-Bromo-1, 3-thiazol-5-yl)methyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2, 3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2, 3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (28 mg, 0.061 mmol) was mixed with c) (4-Bromo-1, 3-thiazol-5-yl)methanol. (2, 4-Dibromo-1, 3-thiazol-5-yl)methanol (0.94 g, 3.44 mmol), sodium carbonate tri-hydrade (1.34 g) and palladium on carbon (10%, 0.07 g) were mixed in methanol (33 mL). The resulting mixture was hydrogenated at 60 psi for 2 days. The solid was filtered off through a pat of celite. The solvent was evaporated and the residue was purified by frash column chromatography to give c (4-Bromo-1, 3-thiazol-5-yl)methanol (2, 4-Dibromo-1, 3-thiazol-5-yl)methanol (0.94 g, 3.44 mmol), sodium carbonate tri-hydrade (1.34 g) and palladium on carbon (10%, 0.07 g) were mixed in methanol (33 mL). The resulting mixture was hydrogenated at 60 psi for 2 days. The solid was filtered off through a pat of celite. The solvent was evaporated and the residue was purified by frash column chromatography to give

Molecular Weight:194.05
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:192.91970
Monoisotopic Mass:192.91970
Topological Polar Surface Area:61.4
Heavy Atom Count:8
Complexity:82.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes