p-Toluenesulfonic acid → HCID 57818943, compound

HRID 705570Notes

Reaction equation

HRID 705570 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.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1>C(O)C1C=CC=CC=1>[CH2:30]([O:19][CH2:18][NH:17][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57818596HCID 57818596, compound

Product 1

HCID 57818943HCID 57818943, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

To a mixture of [5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-ylamino]methanol (0.10 g, 3.7 mmol) in benzyl alcohol (1 mL) was added a catalytic amount of p-toluene sulfonic acid. After 30 min, the reaction was cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The phases were separated and the organic portion was dried over anhydrous Na2SO4, filtered and evaporated to obtain the crude product. Purification by reverse phase chromatography afforded 0.094 g (70%) of the title compound as a white solid: mp 64-66° C.; 1H NMR (CDCl3) δ 7.93 (d, J=2.7 Hz, 1H), 7.47-7.40 (m, 2H), 7.37-7.29 (m, 5H), 7.08-7.00 (m, 2H), 5.81-5.70 (bm, 1H), 5.29 (s, 2H), 5.12 (d, J=6.9 Hz, 2H), 4.63 (s, 2H); MS (ESI) m/z 358 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  2. customThe phases were separated
  3. dry with materialthe organic portion was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain the crude product
  7. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-37b9e290cdbe4cc5a8217450d80b9f48
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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