Sodium Bicarbonate → (S)-2-methyl-propane-2-sulfinic acid ((R)-1-pyrimidin-2-yl-propyl)-amide

HRID 926372Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]=[N:8][S@:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10].[CH2:15]([Mg]Br)[CH3:16].C(=O)([O-])O.[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C@@H:7]([NH:8][S@:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[CH2:15][CH3:16].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C@H:7]([NH:8][S@:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[CH2:15][CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinic acid 1-pyrimidin-2-yl-methylideneamide (18.2 g, 86.1 mmol) in dry tetrahydrofuran at −78° C. was added a 1.0 M solution of ethylmagnesium bromide in tetrahydrofuran (95 ml, 95 mmol) and the mixture was stirred at −78° C. for 45 min. 120 ml of aqueous sodium hydrogencarbonate was added, the mixture was extracted 3 times with dichloromethane (200 ml) and after evaporation of all solvents the crude product was purified by reverse phase HPLC (acetonitrile/water gradient with 0.1% trifluoroacetic acid) to give 1.47 g of (S)-2-methyl-propane-2-sulfinic acid ((S)-1-pyrimidin-2-yl-propyl)-amide (LC/MS (method 5): Rt=2.99 min; m/z=242.21 (M+H+)) and 2.6 g of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-pyrimidin-2-yl-propyl)-amide (LC/MS (method 2): Rt=0.97 min; m/z=242.07 (M+H+)).

Workup

extractionthe mixture was extracted 3 times with dichloromethane (200 ml)
customafter evaporation of all solvents the crude product
customwas purified by reverse phase HPLC (acetonitrile/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-516a04ce8e7f4e7dab3ea57dccd09753
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284333B2

Reaction notes

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