N-(2-aminoethyl)acetamide → HCID 22378694, compound

HRID 895486Notes

Reaction equation

HRID 895486 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[C:15]([NH:18][CH2:19][CH2:20][NH2:21])(=[O:17])[CH3:16].C(N(CC)C(C)C)(C)C>C(O)CC>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([NH:21][CH2:20][CH2:19][NH:18][C:15](=[O:17])[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 77338FenclorimHCID 81531Diisopropylethylamine

Product 1

HCID 22378694HCID 22378694, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

4,6-Dichloro-2-phenylpyrimidine (3) (5.59 g), N-acetylethylenediamine (2.79 g) and N,N-diisopropylethylamine (3.53 g) were added to propan-1-ol (50 ml). A calcium drying tube was fitted and the resulting suspension heated to reflux for 34 hrs, then left to cool to ambient temperature. The resulting solution was evaporated in vacuo onto silica gel (40 g) and purified by flash chromatography eluting with ethyl acetate then a mixture of ethyl acetate and methanol (10:1 v/v) to furnish the title compound (6.79 g).

Workup

  1. customA calcium drying tube was fitted
  2. temperaturethe resulting suspension heated
  3. temperatureto reflux for 34 hrs
  4. waitleft
  5. customThe resulting solution was evaporated in vacuo onto silica gel (40 g)
  6. custompurified by flash chromatography
  7. washeluting with ethyl acetate
  8. additiona mixture of ethyl acetate and methanol (10:1 v/v)

Sources & evidence

ORD record
ord-3f5ab14efc9a4a5dbe1b67bbcc2d768c
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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