Diisopropylethylamine → 2-(2-Amino-6-chloro-5-formyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

Temperature

0 °C

To a 25 mL round bottomed flask cooled to 0° C. was added 2-amino-4,6-di-chloro-5-formyl-pyrimidine (192 mg, 1.0 mmol, 1.0 eq.), THF (10 mL), DIEA (0.34 mL, 2.0 mmol, 2.0 eq.), and 2-amino-N-(3-trifluoromethyl-phenyl)-acetamide (245 mg, 1.0 mmol, 1.0 eq.). The reaction mixture was warmed to RT and allowed to stir overnight before quenching with H2O (10 mL) and EtOAc (50 mL). The EtOAc layer washed with brine, dried with Na2SO4, and concentrated to give crude product as a solid. The solid was then rinsed with 5:95 EtOAc:Hexanes to give pure 2-(2-Amino-6-chloro-5-formyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as a yellow solid (159 mg, 43%). LC/MSD (HP Series 1100 MSD): Expected MW: 373, Observed M+H, 374.0, Retention time: 1.45 min. ANALYTICAL HPLC: >95%, Retention time: 4.15 min (8 minute run). 1H-NMR (d6-DMSO): 10.5 (s, 1H), 9.9 (s, 1H), 9.42 (t, 1H), 8.08 (s, 1H), 7.80 (d, 1H), 7.59 (t, 1H), 7.42 (d, 1H), 4.40 (d, 2H) ppm.

1. temperatureThe reaction mixture was warmed to RT
2. custombefore quenching with H2O (10 mL) and EtOAc (50 mL)
3. washThe EtOAc layer washed with brine
4. dry with materialdried with Na2SO4
5. concentrationconcentrated
6. customto give crude product as a solid
7. washThe solid was then rinsed with 5:95 EtOAc

ORD record

ord-d0166cf424ac4501b1259a32ee72def5

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816353B2