5-Amino-4,6-dichloropyrimidine → (R)-4-chloro-6-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine

HRID 1850681Notes

Reaction equation

CC(C)([O-])C.[Na+].Cl[C:8]1[C:13]([NH2:14])=[C:12]([Cl:15])[N:11]=[CH:10][N:9]=1.[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([OH:23])[CH2:18]1>C1COCC1>[Cl:15][C:12]1[C:13]([NH2:14])=[C:8]([O:23][C@@H:19]2[CH2:20][CH2:21][CH2:22][N:17]([CH3:16])[CH2:18]2)[N:9]=[CH:10][N:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium t-butoxide (586.0 mg, 6.098 mmol) was added to a solution of 4,6-dichloropyrimidin-5-amine (500 mg, 3.049 mmol) and (3R)-1-methylpiperidin-3-ol (351.2 mg, 3.049 mmol) in THF (25.00 mL) at RT. The reaction mixture was heated at 70° C. overnight. The reaction mixture was quenched with 1 mL water and concentrated in vacuo. The residue was extracted with DCM and the combined organic extract were dried and concentrated in vacuo to afford (R)-4-chloro-6-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine which was used in next step without further purification.

Workup

customThe reaction mixture was quenched with 1 mL water
concentrationconcentrated in vacuo
extractionThe residue was extracted with DCM
extractionthe combined organic extract
customwere dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c20624aa64534177880f7e3344e5daa9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957078B2

Reaction notes

Loading…