Ammonium Chloride → HCID 19787913, compound

HRID 1656509Notes

Reaction equation

HRID 1656509 reaction equation
[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:30]([CH3:32])[CH3:31])[CH:17]([O:22][Si](C(C)(C)C)(C)C)[C:18]([F:21])([F:20])[F:19])=[O:14])[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:30]([CH3:31])[CH3:32])[CH:17]([OH:22])[C:18]([F:20])([F:21])[F:19])=[O:14])[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 19787874HCID 19787874, compound

Product 1

HCID 19787913HCID 19787913, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-acetamido-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (0.86 g) in tetrahydrofuran (15 mL) at 0° C. was added tetrabutylammonium fluoride (1.95 mL, 1M in tetrahydrofuran) and the resulting solution was allowed to stir for 5 min. The mixture was poured into saturated aqueous ammonium chloride and the product extracted into ethyl acetate. The organic solution was washed (water), dried, and evaporated. The resulting white solid was collected and washed with ether:hexane to provide 2-(5-acetamido-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-hydroxypropyl)acetamide (0.6 g); NMR: 8.87 (s,1), 8.07 (d,1), 7.57 (m,5), 4.62 (d,1), 4.42 (d,1), 4.10 (m,1), 3.68 (t,1), 2.18 (s,3), 1.80 (m,1), 0.89 (d,3), 0.82 (d,3).

Workup

  1. extractionthe product extracted into ethyl acetate
  2. washThe organic solution was washed (water)
  3. customdried
  4. customevaporated
  5. customThe resulting white solid was collected
  6. washwashed with ether

Sources & evidence

ORD record
ord-5a0cd7e0a8e4419993e4bb4f57cd1502
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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