Guanidine Hydrochloride → 5-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine

HRID 48455

反応式

HRID 48455 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]2[C:15]([NH2:21])=[N:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2COCC[Si](C)(C)C)[CH3:2].CC([O-])(C)C.[K+].C(OC1C=C(C=O)C=C2C=1C=CN2COCC[Si](C)(C)C)C.N(CCC#N)C1C=CC=CC=1.Cl.NC(N)=N>C(O)(C)(C)C.CS(C)=O.C(O)C.O>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]2[C:15]([NH2:21])=[N:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH3:2]

参加物

10

反応物 5

HCID 5742Guanidine HydrochlorideHCID 141003-AnilinopropionitrileHCID 227429264-ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-6-carbaldehydeHCID 23665647Potassium tert-butoxide2 回HCID 699205545-[4-Ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine

生成物 1

HCID 227429195-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine収率 62%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

5-[4-Ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. A warm solution of potassium tert-butylate (900 mg, 8.02 mmol) in tert-butanol (7.5 mL) was added at room temperature to a solution of 4-ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-6-carbaldehyde (2.14 g, 6.69 mmol) and 3-anilinopropionitrile (1.08 g, 7.36 mmol) in methyl sulfoxide (25 mL). After 90 min the solution was treated with water and the suspension formed was stirred for 2 h. The precipitate was collected by filtration and dried. This material was added to a suspension of guanidine hydrochloride (1.90 g, 19.9 mmol) and potassium tert-butylate (2.23 g, 19.9 mmol) in ethanol (100 mL), and the reaction mixture was refluxed for 16 h, then most of the solvent was distilled off, and ether (50 mL) was added. Insoluble material was removed by filtration, the filtrate was washed with water, dried (MgSO4), and evaporated. The residue was washed with diethyl ether/n-hexane 4:3 (70 mL) to afford the title compound (1.71 g, 62%). Light brown solid.

後処理

  1. customthe suspension formed
  2. filtrationThe precipitate was collected by filtration
  3. customdried
  4. temperaturethe reaction mixture was refluxed for 16 h
  5. distillationmost of the solvent was distilled off
  6. additionether (50 mL) was added
  7. customInsoluble material was removed by filtration
  8. washthe filtrate was washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. washThe residue was washed with diethyl ether/n-hexane 4:3 (70 mL)

出典と根拠

ORDレコード
ord-9540ad39a2414b7abb810eca8ddaf9f3
出典データセット
uspto-grants-2004_03
特許番号
US06703397B2

関連ノート

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