Formamidine acetate → HCID 59511330, compound

HRID 1157829Notes

Reaction equation

HRID 1157829 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].CN(C)[CH:10]=[C:11]([N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C>[C:13]1([C:12]2[C:11]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[CH:10][N:7]=[CH:5][N:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 68693760HCID 68693760, compound

Product 1

HCID 59511330HCID 59511330, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of formamidine acetate (2.8 g) in triethylamine (6 ml) in a sealed tube, was added tert-butyl 4-(1-(dimethylamino)-3-oxo-3-phenylprop-1-en-2-yl)piperazine-1-carboxylate (1.0 g) and the reaction mixture was heated at 140° C. for 6 h. The reaction mixture was brought to room temperature and triethylamine was removed under reduced pressure. Water (10 ml) was added to the residue and the organic compound was extracted into ethylacetate (4×20 ml). Combined organic layers were dried (Na2SO4) and concentrated. The crude material was purified by column chromatography using methanol/chloroform (1:9) to give tert-butyl 4-(4-phenylpyrimidin-5-yl)piperazine-1-carboxylate.

Workup

  1. customwas brought to room temperature
  2. customtriethylamine was removed under reduced pressure
  3. additionWater (10 ml) was added to the residue
  4. extractionthe organic compound was extracted into ethylacetate (4×20 ml)
  5. dry with materialCombined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-a2bb3bcdb4674c9280ddeab6346e2d7b
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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