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

HRID 227631

Reaction equation

HRID 227631 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-f20ae985763d49b29e6997f2e3bf926d
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Linked notes

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