Stannous chloride dihydrate → HCID 18516946, compound

HRID 1370093Notes

Reaction equation

HRID 1370093 reaction equation
[C:1]([C:3]1[C:4]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)=[N:7][CH:8]=1)#[N:2].O.O.[Sn](Cl)Cl>C(O)C>[NH2:16][C:12]1[CH:11]=[C:10]([NH:9][C:6]2[N:5]=[C:4]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 18516888HCID 18516888, compound

Product 1

HCID 18516946HCID 18516946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-3-Aminophenyl-5-cyano-4-thien-2-ylpyrimidine-2-amine was prepared by heating a solution of 5-cyano-N-3-nitrophenyl-4-thien-2-ylpyrimidine-2-amine (2.77 g, 8.57 mmol) and tin(II)chloride dihydrate (7.73 g, 34.05 mmol) in ethanol (160 mL) at reflux for 18 h. On cooling the reaction was concentrated under reduced pressure and partitioned between CH2Cl2 and 2M NaOH. The organic phase was dried (MgSO4) and evaporated to give the desired material (320 mg) as a yellow solid, m.p. 221-222°. δH (d6 DMSO) 10.16 (1H, s), 8.83 (1H, s), 8.24 (1H, d, J 3.9 Hz), 7.97 (1H, d, J 5.1 Hz), 7.32 (1H, dd, J 5.0, 4.0 Hz), 6.97 (3H, bm), 6.31 (1H, m) and 5.04 (2H, bs).

Workup

  1. temperatureat reflux for 18 h
  2. temperatureOn cooling the reaction
  3. concentrationwas concentrated under reduced pressure
  4. custompartitioned between CH2Cl2 and 2M NaOH
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f4a2f86685fa459a8ba83ed881e0b6f1
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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