3-Methylpiperidine → 5-Fluoro-4-(3-methylpiperidino)-6-(2-pentynyloxy)pyrimidine

HRID 14521

Reaction equation

Cl[C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14])[N:5]=[CH:4][N:3]=1.[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1>>[F:8][C:7]1[C:2]([N:18]2[CH2:19][CH2:20][CH2:21][CH:16]([CH3:15])[CH2:17]2)=[N:3][CH:4]=[N:5][C:6]=1[O:9][CH2:10][C:11]#[C:12][CH2:13][CH3:14]

Participants

Reactant 2

HCID 790813-Methylpiperidine

HCID 593411204-Chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine

Product 1

HCID 115073805-Fluoro-4-(3-methylpiperidino)-6-(2-pentynyloxy)pyrimidineYield 89%

Procedure

0.2 g of 4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine and 0.29 g of 3-methylpiperidine were mixed and left for 3 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.23 g of 5-fluoro-4-(3-methylpiperidino)-6-(2-pentynyloxy)pyrimidine (hereinafter, referred to as Compound (10)).

Sources & evidence

ORD record: ord-9d3ca9406e9a45a58b25a3f372c9a735
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732448B2

Linked notes

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