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Hydrazine hydrate (1:1) → 2-(2-amino-5-hydrazonomethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

HRID 1160114
ノート
印刷プレビュー

反応式

HRID 1160114 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])[C:5]([CH:23]=O)=[C:4]([S:25][CH3:26])[N:3]=1.O.[NH2:28][NH2:29]>C(O)(C)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])[C:5]([CH:23]=[N:28][NH2:29])=[C:4]([S:25][CH3:26])[N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 111766082-(2-amino-5-formyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

生成物 1

HCID 668603832-(2-amino-5-hydrazonomethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide収率 45.1%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
80 °C

実験手順

To a disposable sealed tube was added 2-(2-amino-5-formyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide (100 mg, 0.25 mmol, 1.0 eq.), isopropanol (4.0 mL), and hydrazine monohydrate (0.048 mL, 0.96 mmol, 3.8 eq.). The tube was sealed and heated to 80° C. overnight. The reaction was then quenched with H2O (10 mL) and EtOAc (50 mL). The EtOAc layer washed with brine, dried with Na2SO4, and concentrated to give crude 2-(2-amino-5-hydrazonomethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as an oil. The crude product was then precipitated out with 3 mL water and 0.5 mL of ACN, filtered and rinsed with 2 mL of H2O to give pure 2-(2-amino-5-hydrazonomethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as a yellow solid (45.0 mg, 45%). LC/MSD (HP Series 1100 MSD): Expected MW: 399, Observed M+H, 400.1, Retention time: 1.43 min. ANALYTICAL HPLC: >90%, Retention time: 3.89 min (8 minute run). 1H-NMR (d6-DMSO): 10.42 (s, 1H), 9.15 (t, 1H), 8.15 (s, 1H), 8.05 (s, 1H), 7.80 (d, 1H), 7.58 (t, 1H), 7.42 (d, 1H), 6.45 (s, 2H), 5.25 (br s, 2H), 4.30 (d, 2H), 2.40 (s, 3H) ppm.

後処理

  1. customThe tube was sealed
  2. customThe reaction was then quenched with H2O (10 mL) and EtOAc (50 mL)
  3. washThe EtOAc layer washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customto give crude 2-(2-amino-5-hydrazonomethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as an oil
  7. customThe crude product was then precipitated out with 3 mL water and 0.5 mL of ACN
  8. filtrationfiltered
  9. washrinsed with 2 mL of H2O

出典と根拠

ORDレコード
ord-e68d1764f79046a68aff04cecbb168f4
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07816353B2

反応ノート

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