Methanol → HCID 10023469, compound

HRID 1785319Notes

Reaction equation

HRID 1785319 reaction equation
[Br:1][C:2]1[C:3]([O:22][CH2:23][C:24]#[CH:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([NH:18][CH2:19][CH2:20][OH:21])[CH:17]=2)[C:12](O)=[O:13])=[N:6][CH:7]=1.C(N(CC)CC)C.[BH4-].[Na+].CO>O1CCCC1>[Br:1][C:2]1[C:3]([O:22][CH2:23][C:24]#[CH:25])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][OH:21])[CH:15]=[C:11]([CH2:12][OH:13])[CH:10]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 57593727HCID 57593727, compound

Product 1

HCID 10023469HCID 10023469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-[(2-hydroxyethyl)amino]benzoic acid and triethylamine (57 μl) in tetrahydrofuran (4 ml) was added ethyl chloroformiate (37 μl) at −10° C. After stirring for 15 minutes at 0° C. sodium borohydride (44 mg) and methanol (3.6 ml) were added and stirring continued over night at room temperature. After dilution with water the reaction mixture was extracted with ethyl acetate and the organic layer subsequently washed with saturated NaHCO3-solution and brine After drying (Na2SO4) and evaporation the residue was subjected to chromatography on-silica gel (hexanes/ethyl acetate) to yield the title compound (59 mg).

Workup

  1. additionwas added ethyl chloroformiate (37 μl) at −10° C
  2. additionwere added
  3. waitcontinued over night at room temperature
  4. extractionAfter dilution with water the reaction mixture was extracted with ethyl acetate
  5. washthe organic layer subsequently washed with saturated NaHCO3-solution and brine
  6. customAfter drying
  7. custom(Na2SO4) and evaporation the residue

Sources & evidence

ORD record
ord-f49c32b0920a4499b5b919e358e164f0
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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