Acetic Acid → HCID 178517559, 화합물

HRID 2036775노트

반응식

HRID 2036775 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 178517559HCID 178517559, 화합물수율 27.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-980bd968c0aa41a7881428819a4535c2
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575184B2

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