Dichloromethane → HCID 86630082, compound

HRID 1692794Notes

Reaction equation

HRID 1692794 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](SC)=[N:8][C:6]=2[N:7]=1.C([Sn](CCCC)(CCCC)[C:24]1[N:25]=[CH:26][S:27][CH:28]=1)CCC.[F-].[Cs+].C(Cl)Cl>CN(C)C=O.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]2[S:10][C:9]([C:24]3[N:25]=[CH:26][S:27][CH:28]=3)=[N:8][C:6]=2[N:7]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 57685391HCID 57685391, compound

Product 1

HCID 86630082HCID 86630082, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-(methylthio)-7-morpholinothiazolo[4,5-d]pyrimidine was combined with 4-(tributylstannyl)thiazole (1.1 eq), cesium fluoride (2 eq), copper iodide (2 eq), tetrakis(triphenylphosphine)palladium (0.1 eq) in dimethylformamide and microwaved 110° C. for 15 minutes. Methylene chloride was added the solution was filtered through silica washing with methanol. The organic layer was evaporated to dryness and the resulting residue was purified by silica gel chromatography to yield 5-chloro-7-morpholino-2-(thiazol-4-yl)thiazolo[4,5-d]pyrimidine as a pale yellow solid.

Workup

  1. custommicrowaved 110° C. for 15 minutes
  2. filtrationwas filtered through silica washing with methanol
  3. customThe organic layer was evaporated to dryness
  4. customthe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e125104f6a71423c81c4f81fb92c6e72
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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