Acetic Acid → HCID 178517559、化合物

HRID 2036775ノート

反応式

HRID 2036775 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 178517559HCID 178517559、化合物収率 27.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-980bd968c0aa41a7881428819a4535c2
出典データセット
uspto-grants-2013_11
特許番号
US08575184B2

反応ノート

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