Water → 5-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

HRID 227631

反応式

HRID 227631 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=O)=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].Cl.Cl[C:20]([NH2:22])=[NH:21].[OH2:23]>COCCOCCOC>[N+:15]([C:12]1[CH:11]=[CH:10][C:9]([C:5]2[C:6]3[C:7]([NH2:8])=[N:21][C:20]([NH2:22])=[N:1][C:2]=3[S:3][CH:4]=2)=[CH:14][CH:13]=1)([O-:17])=[O:23]

参加物

5

反応物 3

HCID 962WaterHCID 3084509Chloroformamidinium chlorideHCID 156061132-Amino-4-(4-nitrophenyl)thiophene-3-carbonitrile

生成物 1

HCID 690630455-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

A suspension of Example 58B (1 g, 4.08 mmol) and chloroformamidine hydrochloride (1.17 g, 10.2 mmol) in diglyme (40 mL) was heated to 130° C. for 15 hours. The mixture was cooled to room temperature, diluted with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was further concentrated under a stream of nitrogen, and purified by silica gel chromatography with 5 to 7% methanol/dichloromethane to provide 0.26 g of the desired product. MS (ESI(+)) m/e 288 (M+H)+.

後処理

  1. extractionextracted twice with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationThe residue was further concentrated under a stream of nitrogen
  7. custompurified by silica gel chromatography with 5 to 7% methanol/dichloromethane

出典と根拠

ORDレコード
ord-f20ae985763d49b29e6997f2e3bf926d
出典データセット
uspto-grants-2009_07
特許番号
US07560552B2

関連ノート

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