Methanol → HCID 10460720, compound

HRID 1656541Notes

Reaction equation

HRID 1656541 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:42][OH:43]>C(O)=O.[Fe]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][CH:42]=[O:43])=[CH:35][CH:34]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 10415744HCID 10415744, compound

Product 1

HCID 10460720HCID 10460720, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Procedure

To a solution of 2-[5-benzyloxycarbonylamino-2-(4-nitrophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (2.02 g) in 90% aqueous formic acid (56 mL) was added iron powder (3.9 g). The mixture was stirred at room temperature overnight. Methanol was added and the reaction mixture filtered through diatomaceous earth to remove the excess iron. Ethyl acetate was added and the resultant solution washed with water (twice), brine, then dried (MgSO4) and evaporated. The crude material was purified by chromatography, with dichloromethane:methanol (gradient, 99.5:0.5, 98.2) as the eluent, followed by trituration with hexane:diethyl ether (80:20), to provide the title compound (1.12 g) as an off-white solid; TLC: Rf =0.39, dichloromethane:acetone (70:30); NMR: 0.67-1.03 (m,6), 2.03-2.33 (m,1), 4.00-4.80 (m,3), 5.17 (s,2), 7.20-7.60 (m,7), 7.57-7.77 (m,2), 8.22 (s,1), 8.43 (s,1), 8.83- 9.07 (m,2), 10.30-10.57 (m,1); MS: m/z=574(M+1).

Workup

  1. filtrationthe reaction mixture filtered through diatomaceous earth
  2. customto remove the excess iron
  3. additionEthyl acetate was added
  4. washthe resultant solution washed with water (twice), brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude material was purified by chromatography, with dichloromethane

Sources & evidence

ORD record
ord-de0a51dd557c47eebeb23ef900e91bfb
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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