Sodium Carbonate → HCID 66550548, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.62 mmol), 3-(hydroxymethyl)phenylboronic acid (104 mg, 0.68 mmol), Pd2(dba)3 (71 mg, 0.12 mmol), X-Phos (118 mg, 0.25 mmol), Na2CO3 (131 mg, 1.2 mmol) in dioxane (20 mL) and H2O (5 mL) was heated to 90° C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by column chromatography (MeOH:DCM=1:80) to give (3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenyl)methanol (51 mg, 21%) as yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 8.49 (s, 1H), 8.42 (d, 1H, J=6.9 Hz), 7.97 (s, 1H), 7.87 (s, 1H), 7.49-7.46 (m, 2H), 7.18 (dd, 1H, J1=8.7 Hz, J2=2.7 Hz), 6.93 (d, 1H, J=8.4 Hz), 4.79 (s, 2H), 4.00 (s, 3H), 3.93 (s, 3H). LC-MS: 395 [M+H]+, tR=1.48 min. HPLC: 98.36% at 214 nm, 98.69% at 254 nm, tR=6.086 min.

Provenance & Evidence