Dichloromethane → HCID 86630082, compound

HRID 1365819Notes

Reaction equation

HRID 1365819 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-e291ccd5a5224835820fc9c900b1fead
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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