Ammonia acetate → 5,6-Dimethyl-2-phenylthieno[2,3-d]pyrimidin-4-amine

HRID 44367

反応式

HRID 44367 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].C(O)(=O)C.[NH3:15].CCO[C:19](OCC)(OCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOC(C)=O>[CH3:9][C:5]1[C:6]2[C:7]([NH2:15])=[N:8][C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:1][C:2]=2[S:3][C:4]=1[CH3:10]

参加物

5

反応物 3

HCID 12432Ammonia acetateHCID 74268Benzene, (triethoxymethyl)-HCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

生成物 1

HCID 252243435,6-Dimethyl-2-phenylthieno[2,3-d]pyrimidin-4-amine収率 31%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-amino-4,5-dimethylthiophene-3-carbonitrile (152 mg, 1.0 mmol), ammonia acetate (308.3 mg, 4.0 mmol) and triethyl orthobenzoate (2.0 mL) in a sealed tube was put in a microwave at 200° C. for 20 min. After the reaction mixture was cooled to room temperature, it was diluted with EtOAc, washed with saturated NaHCO3 and H2O. The solvent was removed by vacuum and the residue was purified by preparative HPLC eluting with acetonitrile and water to give the title compound (80 mg, 31%). 1H NMR (400 MHz, CDCl3) δ2.45 (s, 3H), 2.48 (s, 3H), 5.34 (bs, 2H), 7.46-7.43 (m, 3H), 8.4-8.38 (m, 2H). MS 256 (MH+).

後処理

  1. washwashed with saturated NaHCO3 and H2O
  2. customThe solvent was removed by vacuum
  3. customthe residue was purified by preparative HPLC
  4. washeluting with acetonitrile and water

出典と根拠

ORDレコード
ord-31dbe6461de143a3a798065fdbe430cf
出典データセット
uspto-grants-2013_09
特許番号
US08541421B2

関連ノート

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