Lithium Hydroxide → HCID 85993060, compound

HRID 859110Notes

Reaction equation

HRID 859110 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=1)=O.N(O)=O.C([O:20][C:21]([CH2:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH2:33])=[NH:32])[CH:27]=[CH:28][CH:29]=1)=[O:22])C.[OH-].[Li+]>CC(O)CC>[C:21]([CH2:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]2[N:32]=[C:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=3)[CH:4]=[CH:3][N:33]=2)[CH:27]=[CH:28][CH:29]=1)([OH:20])=[O:22]

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-oneHCID 178470676HCID 178470676, compound

Product 1

HCID 85993060HCID 85993060, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one (1.05 g, 5.0 mmol), 3-ethoxycarbonylmethyl-phenyl-guanidine nitrite (1.42 g, 5.0 mmol), lithium hydroxide (0.12 g, 5.0 mmol) in 2-butanol (15 mL) is heated to reflux for 24 hours. After cooling to room temperature, the solvent is evaporated under reduced pressure. Water (40 mL) is added and extracted with ethyl acetate (2×50 mL). The combined organic layers are dried over sodium sulfate, filtrated and concentrated. The residue is dissolved in ethanol (30 mL) and treated with lithium hydroxide (0.48 g, 20 mmol). The reaction mixture is heated to reflux for 1 hour. After cooling to room temperature, the mixture is concentrated. The residue is dissolved in water and acidified with 10% hydrochloric acid. The solid is collected by filtration and washed with water, methanol and dried to give N-[3-carboxymethyl-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (1.34 g); ESI-MS (m/z): 341.0 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. customthe solvent is evaporated under reduced pressure
  4. additionWater (40 mL) is added
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layers are dried over sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. dissolutionThe residue is dissolved in ethanol (30 mL)
  10. temperatureThe reaction mixture is heated
  11. temperatureto reflux for 1 hour
  12. temperatureAfter cooling to room temperature
  13. concentrationthe mixture is concentrated
  14. dissolutionThe residue is dissolved in water
  15. filtrationThe solid is collected by filtration
  16. washwashed with water, methanol
  17. customdried

Sources & evidence

ORD record
ord-9590e67261db47d69f254de8a8973d52
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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