Triethylamine → (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal

HRID 539015Notes

Reaction equation

[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:24]=[CH:25][N:26]=4)=[CH:18][CH:17]=3)=[C:9]2[N:8]=1)[CH2:4][OH:5].CCN(CC)CC>ClCCl.CS(C)=O.[Cl-].[Na+].O>[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[CH:14][C:15]([C:16]3[CH:17]=[CH:18][C:19]([C:22]4[N:23]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH:24]=[CH:25][N:26]=4)=[CH:20][CH:21]=3)=[C:9]2[N:8]=1)[CH:4]=[O:5]

Participants

Conditions

Temperature: -15 °C

Procedure

To a stirred solution of (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butan-1-ol (0.41 g, 0.83 mmol) in dichloromethane (6 mL) was added Et3N (0.58 mL, 4.2 mmol) at −15° C. A solution of pyridine-sulfur trioxide complex (0.66 g, 4.2 mmol) in DMSO (6 mL) was added in one portion. After stirring at −15° C. for 30 minutes, the mixture was poured into cold brine solution and extracted with ether. The combined organic extracts were washed with brine, dried and concentrated. The residue was purified by column chromatography (5% MeOH in dichloromethane) to give (S)-3-methyl-2-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)butanal (0.36 g, 88%). LCMS (APCI+) m/z 491 [M+H]+.

Workup

extractionextracted with ether
washThe combined organic extracts were washed with brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (5% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-9f7419e12eb744baac93380f4a531a9b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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