Ammonium Hydroxide → 6-{2-Amino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl}-N-[4-(isopropyl)phenyl]pyridine-2-carboxamide

HRID 338699Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:31][CH2:30][C:22]4[N:23]=[C:24](S(C)=O)[N:25]=[CH:26][C:21]=4[CH2:20]3)[N:14]=2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[NH4+:32].[OH-]>O1CCOCC1>[NH2:32][C:24]1[N:25]=[CH:26][C:21]2[CH2:20][N:19]([C:15]3[N:14]=[C:13]([C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=4)=[O:12])[CH:18]=[CH:17][CH:16]=3)[CH2:31][CH2:30][C:22]=2[N:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 6-(2-Methanesulfinyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (4-isopropyl-phenyl)-amide (405 mg, 0.930 mmol) in 1,4-dioxane (10 ml) was treated with NH4OH (3 ml, 28-30%) and the reaction mixture was heated in a sealed tube at 100° C. with stirring for 15 hours. Upon cooling to room temperature, the reaction mixture was concentrated and the residue was taken up in water. The aqueous mixture was extracted with ethyl acetate and the organic extract was dried (MgSO4), filtered, and concentrated. Trituration with MeOH gave the title compound as a yellow, amorphous solid (200 mg, 55%).

Workup

temperatureUpon cooling to room temperature
concentrationthe reaction mixture was concentrated
extractionThe aqueous mixture was extracted with ethyl acetate
extractionthe organic extract
dry with materialwas dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-09b39578523f4e1e90508ee4471f702f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889870B2

Reaction notes

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