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

HRID 2387879Notes

Reaction equation

HRID 2387879 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=2[O:24]C)=[C:4]([CH3:26])[N:3]=1.[CH3:27]O.Cl>C(Cl)Cl.B(Br)(Br)Br.O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:27])=[O:22])=[CH:16][C:15]=2[OH:24])=[C:4]([CH3:26])[N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 684141782-(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetic acid

Product 1

HCID 42613680Methyl 2-(4-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-hydroxyphenyl)acetate

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolventHCID 312751,4-DioxaneSolvent

Procedure

To the product from example 72 step (i) (550 mg) in DCM (20 mL), BBr3 (0.29 ml) was added dropwise and the reaction mixture stirred for 5 h. MeOH (4 mL) was added followed by 4M HCl in dioxane (0.5 mL) and stirred for 16 h and the solvents evaporated. The residue was purified by RPHPLC to give the title compound as a white solid, 8 mg.

Workup

  1. stirringstirred for 16 h
  2. customthe solvents evaporated
  3. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-e79bf078815745d5b3b2e186a5b1a710
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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