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

HRID 227631

반응식

HRID 227631 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8150Diglyme용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-f20ae985763d49b29e6997f2e3bf926d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560552B2

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