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

HRID 1617259Notes

Reaction equation

HRID 1617259 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][CH3:25])=[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[O:24][CH3:25])=[C:8]([CH3:30])[N:7]=1

Participants

7

Reactant 4

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

Product 1

HCID 42613821Methyl 2-(3-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-4-methoxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of boron tribromide (13.95 ml, 1M in DCM) was added portionwise over 30 min to a stirred suspension of the product from example 83 step (iv) (1 g) in DCM (15 mL) at 0° C. The suspension was allowed to warm to rt and stirred for 5 h. The suspension was cooled to 0° C. and then MeOH (10 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 was purified by flash silica chromatography (5% MeOH/DCM) to give the title compound (minor product) as a white solid, 51 mg.

Workup

  1. temperatureThe suspension was cooled to 0° C.
  2. stirringthe mixture stirred for 1 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by flash silica chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-4f235b70136a415e832d69cbeef2cfde
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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