4-Fluorobenzylamine → Benzyl [2-(4-{[(4-fluorophenyl)methyl]carbamoyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl]carbamate

HRID 1161931Notes

Reaction equation

HRID 1161931 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]([C:18]([NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])([CH3:20])[CH3:19])=[N:12][C:11]=1[C:32]([O:34]C)=O)(=O)C1C=CC=CC=1.[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>>[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH:42][C:32]([C:11]2[N:12]=[C:13]([C:18]([NH:21][C:22](=[O:23])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([CH3:20])[CH3:19])[N:14]([CH3:17])[C:15](=[O:16])[C:10]=2[OH:9])=[O:34])=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 17961790HCID 17961790, compound

Product 1

HCID 54725153Benzyl [2-(4-{[(4-fluorophenyl)methyl]carbamoyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl]carbamate

Procedure

To a methanolic solution of methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate, p-fluoro benzylamine (3 eq) was added and mixture was refluxed over night. After evaporation of methanol, residue was taken in EtOAc, washed with 1N HCl and brine, dried (Na2SO4), filtered and evaporated to obtain the title product.

Workup

  1. temperaturemixture was refluxed over night
  2. customAfter evaporation of methanol, residue
  3. washwashed with 1N HCl and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9440f26ce14a4648a52791d70ddf221e
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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