Ethanone, 1-(2-chloro-5-pyrimidinyl)- (9CI)

To a solution of Example 72-1 (15 g, 81.25 mmol, 1.0 eq) in tetrahydrofuran (200 mL) was added hydrochloric acid (1 M, 122 mL, 1.5 eq). The mixture was stirred at 20°C for 2 hours. The mixture was concentrated and the residue partitioned between saturated aqueous sodium bicarbonate (150 mL) and ethyl acetate (100 mL). The organic layer was washed with brine (50 mL * 3), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by colunm chromatography (silica gel, Petroleum ether/Ethyl acetate=10/1 to 5:1) to give the target compound (10 g, 79percent yield) as a light yellow solid. ‘H NMR (400 MHz, CDCl3’) ö 9.10 (s, 2H’), 2.64 (s, 3H’)To a solution of crude 31 (560 rng, 3.0 mrnole) in THF (20 mL) is added aqueous HCI solution (1 M. 5 mL) art room temperature. After stirring at room temperature for 5 hours, the mixture is concentrated and the residue is partitioned between saturated aqueous sodium bicarbonate (20 rnL) and EA (100 mL). The organic layer is washed with brine (20 mL 3), dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (DCM:PE 1 1) to give 32 as a white solid (450 111g. 95percent yield). (MS: [M+H] 157.0)To a solution of l-(2-chloropyrimidin-5-yl)ethanone (1.8 g, 11.5 mmol) in DCM (50 mL) was added DAST (8.0 mL) dropwise at -78 C under nitogen atmosphere. Then the solution was warmed to room temperature for 16 h. The reaction was quenched with ice water (50 mL x 3), extracted with DCM (30 mL x 3). The combined organic layers were washed with brine (50 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE : EtOAc = 20 : 1 to 8 : 1) to give 2495-A (1.4 g, 68%) as a yellow solid. MS 179.1, 181.1 [M+H]+.1. In a microwave oven, 1.000 g (6.387 mmol) of 1- (2-chloropyrimidin-5-yl) ethanone, 1.236g (7.664mmol) (1R, 2S) -2, 6-dimethylindene-1-amineA mixture of 2.476 g (19.161 mmol) of N, N-diisopropylethylamine in 8.0 mL of 1, 4-dioxane was heated at 140 C for 45 minutes.The solvent was removed under reduced pressure, water and dichloromethane were added to the mixture, and the aqueous phase was extracted twice with dichloromethane.The combined organic phases were dried over sodium sulfate, and the solvent was distilled off under reduced pressure. : 50)] purification residue, Yielded 1.630 g (85%)1- (2-{[(1R, 2S) -2, 6-dimethyl-2, 3-dihydro-1H-inden-1-yl] amino} pyrimidin-5-yl) ethanone.N-[(1R, 2S)-2, 6-Dimethyl-2, 3-dihydro-1H-inden-1-yl]-5-[(1E)-N-ethoxyethanimidoyl]pyrimidine-2-amine (ex.:1.103a) and N-[(1R, 2S)-2, 6-dimethyl-2, 3-dihydro-1H-inden-1-yl]-5-[(1Z)-N-ethoxyethanimidoyl]pyrimidine-2-amine (ex.:1.103b) Two batches of 2 g (12.8 mmol) of To a solution of

Molecular Weight:156.57
XLogP3:0.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:156.0090405
Monoisotopic Mass:156.0090405
Topological Polar Surface Area:42.8
Heavy Atom Count:10
Complexity:132
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes