Piperidine → HCID 86624201, compound

HRID 1175726Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]([Cl:16])[C:6]=2[N:7]=1.C(N(C(C)C)C(C)C)C.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:5]2[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]([Cl:16])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2,4,8-trichloropyrido[3,2-d]pyrimidine-6-carboxylate (4.65 g; 15.9 mmol; 1 eq.) (Intermediate 1.3) in acetonitrile (140 mL) was added N-ethyldiisopropyl amine (4 mL; 23.8 mmol; 1.5 eq.). The mixture was cooled down to 0° C. A solution of piperidine (1.57 mL; 15.9 mmol; 1 eq.) in acetonitrile (20 mL) was added dropwise. The mixture was stirred 15 min at 0° C. The mixture was partly concentrated and the precipitate was filtered, washed with MeOH and dried under vacuum to afford methyl 2,8-dichloro-4-(1-piperidinyl)pyrido[3,2-d]pyrimidine-6-carboxylate (Intermediate 1.4) (3.98 g; 73%) as a pink solid in 98.8% HPLC purity; Amount: 3.98 g; Yield: 73%; Formula: C14H14O2Cl2N4; 1H NMR (DMSO-d6) δ 1.71 (sl, 6H), 3.92 (s, 3H), 4.01 (sl, 2H), 4.82 (sl, 2H), 8.42 (s, 1H); LC-MS: M/Z ESI: Rt (min) 2.02; 341.02, 342.89 (M+1); HPLC (H2O TFA 0.1%-ACN TFA 0.05%): Rt (min); Area %=4.27; 98.84.

Workup

concentrationThe mixture was partly concentrated
filtrationthe precipitate was filtered
washwashed with MeOH
customdried under vacuum

Sources & evidence

ORD record: ord-bdeaa9689d824c11808e45ed954a2b77
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842698B2

Reaction notes

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