Pivaloyl chloride → HCID 57818938, compound

HRID 1500018Notes

Reaction equation

HRID 1500018 reaction equation
[F:1][C:2]1[C:3]([NH:17][CH2:18][OH:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>N1C=CC=CC=1>[F:1][C:2]1[C:3]([NH:17][CH2:18][O:19][C:22](=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 57818596HCID 57818596, compound

Product 1

HCID 57818938HCID 57818938, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamino]methanol (0.10 g, 0.37 mmol) in pyridine (2 mL) was added trimethylacetyl chloride (0.048 g, 0.40 mmol), and the mixture was agitated on an orbital shaker at 60° C. for 4 h. The reaction mixture was cooled, evaporated to dryness, and partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered, and evaporated to yield the title compound (0.078 g, 60% yield) as a white solid: mp 134-135° C.; 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=2.5 Hz, 1H), 7.49-7.44 (m, 2H), 7.11-7.03 (m, 2H), 6.17 (bt, J≈7 Hz, 1H), 6.17 (d, J=7.4 Hz, 2H), 5.33 (s, 2H), 1.20 (s, 9H); HPLC-MS m/z 352 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. custompartitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4569b74ed52349d9986a5ad90a9afe42
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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