Sodium Bicarbonate → HCID 58169359, compound

HRID 1484867Notes

Reaction equation

HRID 1484867 reaction equation
[C:1]([O:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[C:9]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[N:23](C(=O)C)[N:22]=2)=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][CH:13]=1)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>CCO>[C:1]([O:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[C:9]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[NH:23][N:22]=2)=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58169362HCID 58169362, compound

Product 1

HCID 58169359HCID 58169359, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of (E)-3-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)allyl acetate (80 mg, 0.192 mmol, 1.0 equiv.) and NaHCO3 (144 mg, 1.724 mmol, 9.0 eqiv.) in EtOH (20 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered, the filtrate was concentrated. The residue was diluted with EtOAc and washed with water, brine, dried (Na2SO4), and filtered. The filtrate was concentrated and purified by silica gel chromatography (EtOAc/MeOH 20:1) to afford (E)-3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)allyl acetate (Compound 81) (8 mg, 11.1%). LC-MS (m/z): 376.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 0.72-0.73 (m, 2H), 0.96-0.98 (m, 2H), 1.91-1.98 (m, 1H), 2.07 (s, 3H), 4.70 (d, J=5.6 Hz, 2H), 6.35 (d, J=15.2 Hz, 1H), 6.46 (s, 1H), 7.10 (d, J=15.2 Hz, 1H), 7.47-7.49 (m, 3H), 8.29-8.30 (m, 2H), 8.54 (s, 1H), 9.29 (s, 1H), 12.16 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel chromatography (EtOAc/MeOH 20:1)

Sources & evidence

ORD record
ord-cb427a7d4bf644e58904ec248c81ba1e
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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