Water → 5-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

HRID 1099101ノート

反応式

HRID 1099101 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11]C(=O)OCC)=S)[C:5]([O:17][CH3:18])=[CH:4][N:3]=1.Cl.[NH2:20]O.C(=O)(O)[O-].[Na+].O>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>[Cl:1][C:2]1[N:7]2[N:11]=[C:9]([NH2:20])[N:8]=[C:6]2[C:5]([O:17][CH3:18])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

生成物 1

HCID 569495765-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine収率 69.6%

試薬・触媒・溶媒 2

HCID 10340Sodium Carbonate触媒HCID 6342Acetonitrile溶媒

実験手順

Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate (2) (290 mg, 1.0 mmol), hydroxylamine hydrochloride (143 mg, 2 eq), and sodium bicarbonate (170 mg, 2 eq) were combined. Water (5 mL) and acetonitrile (5 mL) were added at room temperature. The resulting slurry was stirred at room temperature overnight, then treated with 20 drops of saturated aqueous sodium carbonate solution. The resulting solution was sparged with nitrogen and cooled, producing the product as a chalky precipitate, which was collected by filtration (in two crops), washed with water, and dried to obtain the title compound as a solid (139 mg, 68%): mp 251° C.; 1H NMR (DMSO-d6) δ 7.73 (s, 1H), 3.98 (s 3H); 6.63 (s, 2H); 13C NMR (DMSO-d6): 166.30, 148.14, 128.91, 124.67, 57.51; Mass spec (accurate mass): Calcd for C6H6ClN5O 199.026087; found, 199.0256.

後処理

  1. customThe resulting solution was sparged with nitrogen
  2. temperaturecooled
  3. customproducing the product as a chalky precipitate, which
  4. filtrationwas collected by filtration (in two crops)
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-4b0d709f73a241a9b8afc4f11907afef
出典データセット
uspto-grants-2012_03
特許番号
US08143395B2

反応ノート

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