Sodium Hydroxide → HCID 59020395, compound

HRID 970445Notes

Reaction equation

HRID 970445 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)=[O:15])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1.Cl>[NH2:23][C:19]1[CH:18]=[C:17]([NH:16][C:14]([NH:13][CH2:12][CH2:11][CH2:10][NH:9][C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=2)=[O:15])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59020423HCID 59020423, compound

Product 1

HCID 59020395HCID 59020395, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.71 g (3.98 mmol) of 1-[3-(5-bromo-2-chloro-pyrimidin-4-ylamino)-propyl]-3-(3-nitro-phenyl)-urea in 50 ml of THF is mixed at room temperature with 30 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 24 hours, another 5 ml of the 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid is added. After another 6 hours, the batch is made basic with 2N NaOH solution and extracted from ethyl acetate. The combined organic phases are filtered through a Whatman filter and concentrated by evaporation. The residue that is obtained is purified by chromatography (DCM/EtOH 9:1). 850 mg (2.13 mmol, corresponding to 54% of theory) of the product is obtained.

Workup

  1. waitAfter another 6 hours
  2. extractionextracted from ethyl acetate
  3. filtrationThe combined organic phases are filtered through a Whatman
  4. filtrationfilter
  5. concentrationconcentrated by evaporation
  6. customThe residue that is obtained
  7. customis purified by chromatography (DCM/EtOH 9:1)
  8. custom850 mg (2.13 mmol, corresponding to 54% of theory) of the product is obtained

Sources & evidence

ORD record
ord-ee322f008d20415cb7a4963a90aba65b
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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