Hydrochloric Acid → HCID 57593287, compound

HRID 1785300Notes

Reaction equation

HRID 1785300 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][C:11]#[CH:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([NH2:24])[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].Cl>CO>[CH3:20][O:19][C:17](=[O:18])[C:16]1[CH:21]=[C:22]([NH:24][C:5]2[N:4]=[C:3]([O:9][CH2:10][C:11]#[CH:12])[C:2]([Br:1])=[CH:7][N:6]=2)[CH:23]=[C:14]([NH2:13])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7010431Methyl 3,5-diaminobenzoateHCID 58891029HCID 58891029, compound

Product 1

HCID 57593287HCID 57593287, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5-bromo-2-chloro-4-(prop-2-ynyloxy)pyrimidine (15 g), methyl 3,5-diaminobenzoate (45 g) and concentrated hydrochloric acid (15 ml) in methanol (600 ml) was stirred at 65° C. for 8 h. After concentration to half the volume water was added and the precipitate collected by filtration. The precipitate then was treated with sodium hydroxide solution (1 n) and dichloromethane. The organic phase then was washed with water and brine, dried (Na2SO4) and evaporated to dryness to give the title compound (13.8 g).

Workup

  1. concentrationAfter concentration to half the volume water
  2. additionwas added
  3. filtrationthe precipitate collected by filtration
  4. additionThe precipitate then was treated with sodium hydroxide solution (1 n) and dichloromethane
  5. washThe organic phase then was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5bd4d18dca2e4c3794abb96b4dfe9ef5
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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