Ammonia → 6-Benzyloxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl ester

HRID 458678Notes

Reaction equation

HRID 458678 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH2:21][C:22]([O:24]C)=O)[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[NH3:30]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[NH:30][C:22](=[O:24])[CH2:21][N:9]2[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 184425315-Benzyloxy-2-methanesulfonyl-1-methoxycarbonylmethyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 1359709516-Benzyloxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of intermediate 3, 5-benzyloxy-2-methanesulfonyl-1-methoxycarbonylmethyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester, (1.10 g, 2.59 mmol) in acetonitrile (20 ml) was treated with a freshly prepared solution of ammonia in acetonitrile (20 ml) and the resulting mixture stirred at 22° C. for 2 h. The reaction was monitored by LC/MS and rapid formation of the amino intermediate followed by cyclization was observed. The solvent was then evaporated in vacuo and the residue was diluted with ethyl acetate, washed successively with saturated sodium bicarbonate and brine then dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by recrystallization of the solid residue from ethyl acetate/hexane gave 0.770 g (82% yield) of the title ester as white crystals; mp 196° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (3H, t, J=7.2 Hz, CH3), 4.39 (2H, q, J=7.2 Hz, OCH2), 4.57 (2H, s, CH2), 5.24 (2H, s, OCH2), 7.3–7.55 (5H, m, aromatics), 9.6 (1H, broad, NH). Anal. Calcd for C16H15N3O5: C, 58.35; H, 4.59; N, 12.76. Found: C, 57.99; H, 4.27, N, 12.62.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with saturated sodium bicarbonate and brine
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customfollowed by recrystallization of the solid residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-42cc7ed50c114b6891b7440b210467bd
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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