Triethylamine → Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate

HRID 1409314Notes

Reaction equation

HRID 1409314 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C(#N)C>[O:22]=[C:19]1[CH2:20][CH2:21][N:3]2[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]2[NH:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178469899HCID 178469899, compound

Product 1

HCID 136377291Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylateYield 26.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 2-amino-1H-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethylamine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0° C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50° C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, 1H), 8.78 (bs, 1H).

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was slowly warmed to RT
  3. temperaturesubsequently heated to 50° C. for 16 h
  4. customThe solvent was evaporated
  5. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-93ea860b822e443a8d91d9573bf65bef
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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