Water → HCID 67446055, compound

HRID 1396173Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[C:24]4[C:23]([O:25][CH2:26][CH3:27])=[N:22][CH:21]=[N:20][C:19]=4[NH:18][CH:17]=3)=[C:11]([F:28])[N:10]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.O>O1CCCC1>[CH2:26]([O:25][C:23]1[C:24]2[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:5]4[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=4)=[N:10][C:11]=3[F:28])=[CH:17][NH:18][C:19]=2[N:20]=[CH:21][N:22]=1)[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

To (6-bromo-pyridin-3-yl)-[5-(4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-6-fluoro-pyridin-2-yl]-amine (P-4020, 0.040 g, 0.090 mmol) in 5.0 mL of tetrahydrofuran under nitrogen at −78° C., tert-butyllithium (0.531 mL, 1.70 M in hexane, 0.903 mmol) is added. The reaction is stirred at −78° C. for 30 minutes, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified with silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-4021, 25.7 mg). MS (ESI) [M+H+]+=364.9.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under vacuum
customThe resulting material is purified with silica gel column chromatography
washeluting with 20-100% ethyl acetate in hexane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6e1b547e42544a679fd07d65ded9d7ce
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901118B2

Reaction notes

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