Acetic Acid → HCID 135578122, compound

HRID 1638605Notes

Reaction equation

HRID 1638605 reaction equation
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:22])[C:8]([CH2:18][CH2:19][CH:20]=O)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2].[NH2:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:22])[C:8]([CH2:18][CH2:19][CH2:20][NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:33][CH:34]=2)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2337BenzocaineHCID 5003444Sodium cyanoborohydrideHCID 135578121HCID 135578121, compound

Product 1

HCID 135578122HCID 135578122, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.25 g (4.00 mmol) of 3-[2-(acetylamino)-4-(diacetylamino)-1,6-dihydro-6-oxo-5-pyrimidinyl]propionaldehyde, 0.743 g (4.50 mmol) of ethyl p-aminobenzoate, 1.0 ml of glacial acetic acid, and 3A molecular sieves in 25 ml of methanol was stirred at room temperature for 3 hours under nitrogen before 0.28 g (4.47 mmol) of sodium cyanoborohydride was added during a 2 minute period. After stirring for 17 hours, the mixture was filtered. The filtrate was spin evaporated in vacuo to a yellow foam. The product was separated from a mixture by flash chromatography on Silica Gel 60 (100 g; 230-400 mesh, EM Reagents) with ethyl acetate. Appropriate fractions were combined on the basis of TLC correlation, and solent was removed by spin evaporation in vacuo. Recrystallization from ethyl acetate yielded 0.44 g (24% of theory) of ethyl 4-[3-[2-(acetylamino)-4-(diacetylamino)-1,6-dihydro-6-oxo-5-pyrimidinyl]propylamino]benzoate as a white solid, mp 197°-198°; TLC (ethyl acetate), Rf =0.5; NMR (DMSO-d6) δ 1.28 (t, J=7.1 Hz, 3H, CH3), 1.65 (m, 2H, CCH2C), 2.14 (s, 3H, Ac), 2.2 (m, 2H, CH2Het), 2.23 (s, 6H, 2Ac), 3.05 (m, 2H, CH2N), 4.22 (q, J=7.1 Hz, 2H, CO2CH2), 6.5 (br, 1H, AcNH obscured by Ar), 6.57 (d, 2H, ArH), 7.69 (d, 2H, ArH). Elemental analysis. Calculated for C22H27N5O6, 0.5 H2O (MW 466.49): C, 56.64; H, 6.05; N, 15.01. Found: C, 56.88; H, 6.01; N, 14.88.

Workup

  1. additionwas added during a 2 minute period
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo to a yellow foam
  4. customThe product was separated from a mixture by flash chromatography on Silica Gel 60 (100 g; 230-400 mesh, EM Reagents) with ethyl acetate
  5. customsolent was removed by spin evaporation in vacuo
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fd61d236c551469a95ad0fe3da7aadc5
Source dataset
uspto-grants-1989_11
Patent number
US04880812

Reaction notes

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