Methanol → HCID 11630104, compound

Participants

Reaction Conditions

Reaction Steps

[4-(1-piperidinyl)pyrido[3,2-d]pyrimidin-6-yl]methanol (Intermediate 1.6) (3.95 g; 16.2 mmol; 1.00 eq.) was dissolved in DCM (160 mL). The solution was cooled down to 0° C. and manganese oxide (16.5 g; 0.162 mol; 10 eq.) was added. The reaction was stirred 5 min at 0° C. then overnight at rt. To complete the conversion, MnO2 was added after 12 hours and 20 hours (two batches of 4.96 g; 48.48 mmol; 3 eq.). After 20 hours, the reaction was complete. MeOH (100 mL) was added and the mixture was filtered through Celite, and widely rinsed with DCM/MeOH 1:1 mixture. Solvents were removed under reduced pressure to give 4-(1-piperidinyl)pyrido[3,2-d]pyrimidine-6-carbaldehyde (Intermediate 1.7). This product was used in the next step without further purification. Amount: 4.1 g; Formula: C13H14ON4; HPLC Purity: 58.84%; LC-MS: M/Z ESI: Rt (min) 1.53; 243.06 (M+1); HPLC (H2O TFA 0.1%-ACN TFA 0.05%): Rt (min); Area %=1.39; 58.84. 1H NMR (DMSO-d6) δ 9.95 (s, 1H), 8.52 (s, 1H), 8.16 (m, 2H), 4.46 (1, 4H), 1.70 (1, 6H).

Provenance & Evidence