Hydrochloric Acid → (E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amine

HRID 1464981Notes

Reaction equation

HRID 1464981 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1/[CH:4]=[CH:5]/[C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=2[S:8][CH:7]=1.O.O.Cl[Sn]Cl.Cl.[NH4+].[OH-].C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[NH2:20][C:17]1[CH:18]=[CH:19][C:2]([CH3:1])=[C:3]([CH:16]=1)/[CH:4]=[CH:5]/[C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=2[S:8][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 61436Stannous chloride dihydrateHCID 53357563(E)-7-(2-methyl-5-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine

Product 1

HCID 67359028(E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amineYield 95.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-7-(2-methyl-5-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine (0.3 g, 0.96 mmol) was dissolved in ethyl acetate (5 mL) and then SnCl2.2H2O (1 g, 4.81 mmol) and conc. HCl (0.5 mL) were added thereto, and the reaction mixture was stirred at room temperature for 18 hours. After the reaction was completed NH4OH solution was added thereto to pH 5. Then, anhydrous Na2CO3 was added thereto to pH 7. The reaction mixture was filtered with Celite and washed with ethyl acetate several times. The filtrate was concentrated under reduced pressure to obtain the title compound (260 mg, 84% yield) without further purification.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered with Celite
  3. washwashed with ethyl acetate several times
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d9b2d6f13d55416b84eb8a8676e51ad6
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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