Hydrochloric Acid → Methyl 2-(3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-hydroxyphenyl)acetate

HRID 2387912Notes

Reaction equation

HRID 2387912 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([CH2:17][C:18]2[CH:19]=[C:20]([CH2:26][C:27]([OH:29])=[O:28])[CH:21]=[CH:22][C:23]=2[O:24]C)=[C:8]([CH3:30])[N:7]=1.[CH3:31]O.Cl>C(Cl)Cl.O1CCOCC1>[NH2:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([CH2:17][C:18]2[CH:19]=[C:20]([CH2:26][C:27]([O:29][CH3:31])=[O:28])[CH:21]=[CH:22][C:23]=2[OH:24])=[C:8]([CH3:30])[N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25134Boron tribromide2×HCID 689520622-(3-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxyphenyl)acetic acid

Product 1

HCID 42613885Methyl 2-(3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of boron tribromide (2.51 ml, 1M in DCM) was added portionwise over 30 min to a stirred suspension of the product from example 83 step (iv) (300 mg) in DCM (5 mL) at 0° C. The suspension was allowed to warn to rt and stirred for 3 h. A further portion of boron tribromide (1.674 ml, 1M in DCM) was added and the mixture stirred at rt for a further 2 h. MeOH (2 mL) and 4M HCl in dioxane (2 mL) were added and the mixture stirred for 1 h. The solvent was evaporated under reduced pressure and the residue purified by RPHPLC, to give the title compound as a white solid, 27 mg.

Workup

  1. customto warn to rt
  2. stirringthe mixture stirred at rt for a further 2 h
  3. stirringthe mixture stirred for 1 h
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-04126f2eaeea4aa295c4bad7021e9bf0
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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