Hydrochloric Acid → 1-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]piperidin-4-amine
Reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[N:11]=[C:10]([N:19]2[CH2:24][CH2:23][CH:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH2:20]2)[N:9]=1.Cl.C(=O)(O)[O-].[Na+]>CO.O1CCOCC1>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:16])=[O:17])[N:11]=[C:10]([N:19]2[CH2:20][CH2:21][CH:22]([NH2:25])[CH2:23][CH2:24]2)[N:9]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-Butyl N-[1-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-4-piperidyl]carbamate (1.30 g, 2.77 mmol) was dissolved in methanol (10 mL). 4M Hydrochloric acid in dioxane (10 mL) was added. The reaction was stirred at RT for 3 hours. Saturated aqueous sodium bicarbonate was added until pH7 was reached and the organic solvents were removed in vacuo. Water (20 mL) was added and the product was extracted into ethyl acetate (50 mL). The aqueous layer was extracted with a second portion of ethyl acetate (25 mL). The combined organics were evaporated to give the desired material as a yellow foam (1.05 g).
Workup
- customthe organic solvents were removed in vacuo
- additionWater (20 mL) was added
- extractionthe product was extracted into ethyl acetate (50 mL)
- extractionThe aqueous layer was extracted with a second portion of ethyl acetate (25 mL)
- customThe combined organics were evaporated
Sources & evidence
- ORD record
- ord-2f678d16e7dd49228156f15b755afa38
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750003B2
Reaction notes
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