Acetic Acid → HCID 178517559, compound

HRID 2036775Notes

Reaction equation

HRID 2036775 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)=[NH:4].[NH2:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[C:13]=1[C:14]([OH:16])=O.C(O)(=O)C>CO>[Br:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:12]2[C:13]=1[C:14]([OH:16])=[N:4][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1)=[N:11]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 105606492-Amino-6-bromobenzoic acidHCID 45080301Methyl pyrimidine-5-carboximidate

Product 1

HCID 178517559HCID 178517559, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of methylpyrimidine-5-carbimidate (2.00 g, 14.5 mmol) in methanol (20 mL) was added 2-amino-6-bromobenzoic acid (3.1 g, 14.5 mmol). The mixture was heated to reflux where it stirred for 16 h under the nitrogen atmosphere. At the conclusion of this period, acetic acid (2.72 ml, 47 mmol) was added drop wise. Upon completion of addition, methanol was evaporated under reduced pressure to yield a residue. The residue was triturated with ether (100 mL), ethyl acetate (50 mL) and the resulting solid was dried to yield 5-bromo-2-(pyrimidin-5-yl)quinazolin-4-ol (1.2 g, 27%) as an off-white solid. The crude product was used without further purification. 1H NMR (400 MHz, DMSO-d6, δ): 7.64 (dd, J=7.2 Hz, 8.4 Hz, 1H); 7.73-7.75 (m, 2H); 9.35 (s, 1H); 9.46 (s, 2H); 12.9 (br s, 1H). ES-MS: [M++1]=303 and [M++3]=305.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux where it
  3. customwas evaporated under reduced pressure
  4. customto yield a residue
  5. customThe residue was triturated with ether (100 mL), ethyl acetate (50 mL)
  6. customthe resulting solid was dried

Sources & evidence

ORD record
ord-980bd968c0aa41a7881428819a4535c2
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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