Tin tetrachloride → HCID 21109095, compound

HRID 1435710Notes

Reaction equation

HRID 1435710 reaction equation
[C:1]([C:3]1[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)=[N:5][C:6]([S:24][CH3:25])=[N:7][C:8]=1[CH2:9][CH2:10][CH:11](C(OCC)=O)[C:12]([O:14][C:15](C)([CH3:17])C)=[O:13])#[N:2].Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[NH2:2][C:1]1[C:3]2[C:4]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=3)=[N:5][C:6]([S:24][CH3:25])=[N:7][C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:17])=[O:13]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 86614568HCID 86614568, compound

Product 1

HCID 21109095HCID 21109095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ethyl {2-[5-cyano-2-methylthio-4-(3-nitro-phenyl)-pyrimidin-6-yl]-ethyl}-malonate (example 27c, 1.40 g) in CH2Cl2 (15 ml) was cooled to 0° C. A solution of SnCl4 (1 M in CH2Cl2, 11.5 ml) was added dropwise, the ice-bath removed and the solution was stirred for an additional 30 min at room temperature. Water (64 ml) and EtOAc (64 ml) were added and the mixture was vigorously stirred until al solids dissolved. The organic phase was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure, giving the title compound as a crude product.

Workup

  1. customthe ice-bath removed
  2. additionWater (64 ml) and EtOAc (64 ml) were added
  3. stirringthe mixture was vigorously stirred until al solids
  4. dissolutiondissolved
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6045732b2ba04ef39bf56092a217d107
Source dataset
uspto-grants-2009_11
Patent number
US07618963B2

Reaction notes

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