Sodium percarbonate → HCID 23634345, compound

HRID 2039674Notes

Reaction equation

HRID 2039674 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]#[N:29])[CH:23]=3)=[CH:17][C:16]=2[F:30])=[O:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:32].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>CC(C)=O.O>[C:1]([C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:13])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([NH2:29])=[O:32])[CH:23]=3)=[CH:17][C:16]=2[F:30])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159762Sodium percarbonateHCID 23634344HCID 23634344, compound

Product 1

HCID 23634345HCID 23634345, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(6-tert-butylpyrimidin-4-yl)-3-[4-(2-cyanopyridin-4-yloxy)-2-fluoro-phenyl]urea (141 mg, 0.35 mmol) and sodium percarbonate (with 25% H2O2) (218 mg, 1.4 mmol, 4.0 eq) in 2:1 v/v acetone/water (11 mL) was stirred at 60° C. for 16 h. The reaction was partitioned between ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. Trituration from methanol afforded the title compound (63 mg, 43%) as a white solid. 1H-NMR (DMSO-d6) 10.32 (broad s, 1H), 10.08 (broad s, 1H), 8.75 (d, J=1.2 Hz, 1H), 8.51 (d, J=5.4 Hz, 1H), 8.23 (t, J=9.3 Hz, 1H), 8.12 (broad s, 1H), 7.71 (broad s, 1H), 7.61 (d, J=1.2 Hz, 1H), 7.40 (d, J=2.4 Hz, 1H), 7.36 (dd, J=11.4, 2.4 Hz, 1H), 7.18 (dd, J=5.7, 2.7 Hz, 1H), 7.08 (ddd, J=9.0, 2.7, 1.5 Hz, 1H), 1.26 (s, 9H); LC-MS m/z 425 [M+H]+, RT=3.16 min.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2cb5edff17d748a3bfa85794b756f8f9
Source dataset
uspto-grants-2013_11
Patent number
US08580798B2

Reaction notes

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