Potassium Carbonate → HCID 73504502, compound

HRID 1478577Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:22][N:21]([C:23]5[N:28]=[CH:27][C:26]([OH:29])=[CH:25][N:24]=5)[CH2:20][CH2:19][O:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:18][CH2:19][CH2:20][N:21]([C:23]5[N:24]=[CH:25][C:26]([O:29][CH2:32][CH2:33][N:34]6[CH2:39][CH2:38][O:37][CH2:36][CH2:35]6)=[CH:27][N:28]=5)[CH2:22]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

(S)-2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-ol 26 mg (0.066 mmol) was dissolved in DMF 2 ml, and 4-(2-chloroethyl)morpholinehydrochloride 14.8 mg (0.079 mmol) and potassium carbonate 28 mg (0.19 mmol) were added, followed by stirring at 80° C. overnight. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(2-morpholinoethoxy)pyrimidin-2-yl)morpholine 5 mg (15%).

Workup

customAfter the completion of the reaction
extractionthe reaction mixture was extracted with H2O, EA, and brine
customby drying
filtration(Na2SO4), filtration, and concentration under reduced pressure
customthe residue was purified by column chromatography (MeOH:MC=1:10)

Sources & evidence

ORD record: ord-45967d70b993482a8ced936acd45273e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

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