Formaldehyde → Ethyl 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate

HRID 1158848Notes

Reaction equation

HRID 1158848 reaction equation
[CH3:1]CN(CC)CC.C=O.[BH3-]C#N.[Na+].Cl.[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]2[CH2:27][NH:26][CH2:25][CH2:24][N:23]2[CH:28]=1)=[O:19])[CH3:16]>C(Cl)Cl.CO>[CH2:15]([O:17][C:18]([C:20]1[N:21]=[C:22]2[CH2:27][N:26]([CH3:1])[CH2:25][CH2:24][N:23]2[CH:28]=1)=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 11845779HCID 11845779, compound

Product 1

HCID 11845248Ethyl 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Et3N (3.44 mL), 37% HCHO aq. (2.02 mL) and NaBH3CN (1.78 g) were added successively to the MeOH (75 mL) solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester, hydrochloride (5.2 g) at room temperature and stirred for 3.5 h under a nitrogen atmosphere. The mixture was diluted with CH2Cl2 and washed with 50% K2CO3 aq. The organic layer was dried (K2CO3) and filtered. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with CHCl3-acetone (1/1˜1/2). The titled compound was obtained as orange oil. Yield: 2.68 g, 57%).

Workup

  1. washwashed with 50% K2CO3 aq. The organic layer
  2. dry with materialwas dried (K2CO3)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. washthe column was eluted with CHCl3-acetone (1/1˜1/2)

Sources & evidence

ORD record
ord-8f1aa6a728a74c6ead40c105b355a49f
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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