Glycine → HCID 21948244, compound

HRID 2214487Notes

Reaction equation

HRID 2214487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].O>C1CCN2C(=NCCC2)CC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:22][CH2:23][C:24]([OH:26])=[O:25])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 962WaterHCID 9905031N-(3-chlorophenyl)-4-(2-chloropyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 21948244HCID 21948244, compound

Reagents, catalysts & solvents 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) and glycine (4.8 g, 0.06 ml) in DBU (100 ml) is heated at 150° C. under an atmosphere of argon for 40 hours. The still hot reaction mixture is poured into water. After washing the aqueous phase with ethyl acetate the pH is adjusted to 5 by adding citric acid. The resulting precipiate is filtered and recrystallized from dimethylformamide/ethanol to give the product in form of yellow crystals, m.p. 136–138° C. (with decomposition).

Workup

  1. washAfter washing the aqueous phase with ethyl acetate the pH
  2. additionby adding citric acid
  3. filtrationThe resulting precipiate is filtered
  4. customrecrystallized from dimethylformamide/ethanol
  5. customto give the product in form of yellow crystals, m.p. 136–138° C. (with decomposition)

Sources & evidence

ORD record
ord-a9c540219bf6449e8e03def5bc7bb29b
Source dataset
uspto-grants-2006_09
Patent number
US07109197B2

Reaction notes

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