2-Amino-4-methylpyridine → HCID 90067537, compound

HRID 1057040Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[C:4]([N:21]([CH2:23][CH2:24][OH:25])[CH3:22])[N:3]=1.[CH3:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[CH:28]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1>O1CCOCC1>[OH:25][CH2:24][CH2:23][N:21]([CH3:22])[C:4]1[CH:5]=[C:6]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH:9]=2)[CH:7]=[C:2]([NH:33][C:29]2[CH:28]=[C:27]([CH3:26])[CH:32]=[CH:31][N:30]=2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of tert-butyl 4-(2-chloro-6-(2-hydroxyethyl(methyl)amino)-4-pyridyl)-5,6-dihydro-2H-pyridine-1-carboxylate (220 mg, 0.60 mmol), 4-methylpyridin-2-amine (71.13 mg, 0.66 mmol), sodium tert-butoxide (86.2 mg, 0.90 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (34.9 mg, 0.075 mmol), and RuPhos palladium(II) phenethylamine chloride (43.6 mg, 0.06 mmol) in 1,4-dioxane (3.0 mL) was capped in a small CEM microwave vial, de-gassed with N2, and heated in microwave at 120° C. for 15 min. It was concentrated onto Celite, purified by column chromatography (ISCO), 12 g column, eluded with 0-5% MeOH/DCM to give 135 mg (51%) of the title compound as a yellow gum. LC-MS: m/z=440 (M+H+).

Workup

customwas capped in a small CEM microwave vial
customde-gassed with N2
concentrationIt was concentrated onto Celite
custompurified by column chromatography (ISCO), 12 g column

Sources & evidence

ORD record: ord-66209f1c429c4c1f928e1127199fa3e8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399636B2

Reaction notes

Loading…