Sodium Carbonate → HCID 86696720, compound

HRID 2365864Notes

Reaction equation

HRID 2365864 reaction equation
[CH:1]12[CH2:39][CH:4]([CH:5]([NH:7][C:8]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][N:17]([C@@H:20]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([F:37])[CH:31]=5)[CH2:21][O:22][Si](C(C)(C)C)(C)C)[C:16](=[O:38])[CH:15]=4)[CH:11]=[CH:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2.C([O-])([O-])=O.[Na+].[Na+]>Cl.CO>[CH:1]12[CH2:39][CH:4]([CH:5]([NH:7][C:8]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][N:17]([C@@H:20]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([F:37])[CH:31]=5)[CH2:21][OH:22])[C:16](=[O:38])[CH:15]=4)[CH:11]=[CH:10][N:9]=3)[CH2:6]1)[CH2:3][O:2]2

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 86696719HCID 86696719, compound

Product 1

HCID 86696720HCID 86696720, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The crude 4-(2-(2-oxabicyclo[2.2.1]heptan-5-ylamino)pyrimidin-4-yl)-1-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)pyridin-2(1H)-one was dissolved in a solution of HCl in methanol (5 mL, 1M). After being stirred at room temperature for 2 hours, the reaction mixture was then adjusted to pH around 8 by saturated Na2CO3. The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by prep-HPLC to afford 4-(2-(2-oxabicyclo[2.2.1]heptan-5-ylamino)pyrimidin-4-yl)-1-((S)-1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl)pyridin-2(1H)-one (23 mg, 29% yield). 1H NMR (500 MHz, CD3OD) δ 8.42 (d, J=5.0 Hz, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.51 (t, J=16 Hz, 1H), 7.35□7.33 (m, 1H), 7.29 (s, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.14 (d, J=5.5 Hz, 1H), 7.08-7.06 (m, 1H), 6.15-6.13 (m, 1H), 4.40 (s, 1H), 4.32-4.28 (m, 1H), 4.22-4.19 (m, 1H), 4.09-4.07 (m, 1H), 3.71-3.69 (m, 1H), 3.61 (d, J=7.0 Hz, 1H), 2.69 (s, 1H), 2.19 (t, J=12.0 Hz, 1H), 1.86 (d, J=10.5 Hz, 1H), 1.66 (d, J=10.0 Hz, 1H), 1.58 (d, J=14.0 Hz, 1H); LCMS (ESI) m/z: 571.3 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-55d0e55665134995bcb7c67d1ab846a4
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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