Stannous chloride dihydrate → 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

HRID 1398503ノート

反応式

HRID 1398503 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[N:10]=2)[CH:7]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:16][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[N:10]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 681819124-N-(5-bromo-2-nitrophenyl)pyrimidine-2,4-diamine

生成物 1

HCID 681818104-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
65 °C

実験手順

To a solution of 4-N-(5-bromo-2-nitrophenyl)pyrimidine-2,4-diamine (5.06 g, 16.32 mmol) in ethanol (110 mL) was added tin(II) chloride dihydrate (12.89 g, 57.11 mmol). The reaction mixture was stirred at 65° C. for 2 hr. The reaction mixture was evaporated to dryness and ice-water added. The pH of the mixture was adjusted to 10 using saturated aqueous Na2CO3 solution. EtOAc was added followed by saturated aqueous Rochelles salt (potassium sodium tartrate). The resulting mixture was stirred until separate layers were observed. The organic layer was extracted and the extraction repeated (2×) with EtOAc and DCM. Combined organic layer were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a pale yellow solid: 1H NMR (250 MHz, DMSO) δ 5.05 (2H, br. s), 5.79 (1H, d, J=5.79 Hz), 6.08 (2H, br. s), 6.68 (1H, d, J=8.53 Hz), 7.02 (1H, dd, J=8.60, 2.36 Hz), 7.36 (1H, d, J=2.28 Hz), 7.75 (1H, d, J=5.63 Hz), 8.15 (1H, s); LC-MS: m/z=+279.9, 281.9 (M+H)+.

後処理

  1. customThe reaction mixture was evaporated to dryness and ice-water
  2. additionadded
  3. additionEtOAc was added
  4. stirringThe resulting mixture was stirred
  5. customuntil separate layers
  6. extractionThe organic layer was extracted
  7. extractionthe extraction
  8. washCombined organic layer were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8fc6cfd792eb47a19f25c5a802ce3007
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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