4-Chloro-2,6-di(pyrrolidin-1-yl)pyrimidine → HCID 18981248, compound

HRID 1441140Notes

Reaction equation

HRID 1441140 reaction equation
ClC1N=C([NH:8][CH2:9][CH2:10][S:11]([OH:14])(=[O:13])=[O:12])C=C(Cl)N=1.Cl[C:17]1[CH:22]=[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:20]=[C:19]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[N:18]=1>>[N:28]1([C:19]2[N:18]=[C:17]([NH:8][CH2:9][CH2:10][S:11]([OH:14])(=[O:13])=[O:12])[CH:22]=[C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:20]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 7036994-Chloro-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 18981255HCID 18981255, compound

Product 1

HCID 18981248HCID 18981248, compound

Procedure

The 2-(2,6-dichloropyrimidin-4-ylamino)ethanesulfonic acid (III, EXAMPLE 97, 3.0 g) is dissolved in pyrrolidine (IV, 125 ml) and heated to reflux. Solvent evaporation gives a semisolid which is chromatographed on 155 g of silica gel eluting with chloroform/3.9M ammonia in methanol (7/3). An initial fraction of 150 ml is collected followed by 15 ml fractions. Fractions 8-18 contained the desired product. Solvent evaporation and drying under high vacuum gives a solid (a portion of which) is rechromatographed on 155 g silica gel and eluting with the same solvent system as described above. The appropriate fractions are pooled and concentrated to give the title compound, which is used in subsequent reactions without further purification.

Workup

  1. temperatureheated to reflux
  2. customSolvent evaporation
  3. customgives a semisolid which
  4. customis chromatographed on 155 g of silica gel eluting with chloroform/3.9M ammonia in methanol (7/3)
  5. customAn initial fraction of 150 ml is collected
  6. customSolvent evaporation
  7. customdrying under high vacuum
  8. customgives a solid (a portion of which)
  9. customis rechromatographed on 155 g silica gel
  10. washeluting with the same solvent system
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-887024aaa6dc450d9ec7752242934818
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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