4-Fluorobenzylamine → HCID 178511399, compound

HRID 1013001Notes

Reaction equation

HRID 1013001 reaction equation
C([O:9][C:10]1[C:11]([C:35]([O:37]C)=O)=[N:12][C:13]([CH:17]([NH:27]C(OC(C)(C)C)=O)[CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:14][C:15]=1[OH:16])(=O)C1C=CC=CC=1.[F:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1>>[NH2:27][CH:17]([C:13]1[N:12]=[C:11]([C:35]([NH:45][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([F:39])=[CH:41][CH:42]=2)=[O:37])[C:10]([OH:9])=[C:15]([OH:16])[N:14]=1)[CH2:18][O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 178499093HCID 178499093, compound

Product 1

HCID 178511399HCID 178511399, compound

Procedure

To a methanolic solution of methyl 5-(benzoyloxy)-2-{2-(benzyloxy)-1-[(tert butoxycarbonyl)amino]ethyl}-6-hydroxypyrimidine-4-carboxylate prepared as described in Step 2, 4-fluorobenzylamine (2.15 eq.) was added. The resulting solution was refluxed for 24 hours (100% conversion by LC-MS). After cooling to room temperature, the crude was concentrated under reduced pressure and the solvent switched to CH2Cl2. To the solution, trifluoroacetic acid was added and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated and diethyl ether (100 mL) was added. The resulting slurry was stirred for 1 hour at room temperature and the product was collected by filtration. The cake was washed with cold diethyl ether and dried under reduced pressure to afford title compound as trifluoroacetic salt. MS (ES) C21H21FN4O4 requires 412. Found: 413.

Workup

  1. additionwas added
  2. temperatureThe resulting solution was refluxed for 24 hours (100% conversion by LC-MS)
  3. concentrationthe crude was concentrated under reduced pressure
  4. additionTo the solution, trifluoroacetic acid was added
  5. concentrationThe reaction mixture was concentrated
  6. additiondiethyl ether (100 mL) was added
  7. stirringThe resulting slurry was stirred for 1 hour at room temperature
  8. filtrationthe product was collected by filtration
  9. washThe cake was washed with cold diethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f94c07d7effe4bc2a0b01e7aa438a69d
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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