1-(Pyrimidin-2-yl)thiourea → HCID 46836790, compound

HRID 2366494Notes

Reaction equation

HRID 2366494 reaction equation
Br[C:2]1(Br)[CH2:10][C:9]([CH3:12])([CH3:11])[C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]1=O.[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[NH:21][C:22]([NH2:24])=[S:23]>C(O)C>[CH3:11][C:9]1([CH3:12])[C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:3]2[N:24]=[C:22]([NH:21][C:16]3[N:17]=[CH:18][CH:19]=[CH:20][N:15]=3)[S:23][C:2]=2[CH2:10]1

Participants

4

Reactant 2

HCID 27605161-(Pyrimidin-2-yl)thioureaHCID 67457300HCID 67457300, compound

Product 1

HCID 46836790HCID 46836790, compoundYield 1,477,832.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to Scheme 2 Step 4: A solution of 5,5-dibromo-7,7-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one (6.09 mmol, 1.96 g) and of 1-(pyrimidin-2-yl)thiourea (6.09 mmol, 939 mg) in ethanol (18 mL) was microwaved at 150° C. for 90 minutes and then at 140° C. for 40 minutes. After filtration, the reaction mixture was concentrated to dryness. The crude residue was partitioned between DCM and a saturated solution of Na2CO3. The aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4 and concentrated. The crude residue was purified by flash chromatography over silica gel using DCM/MeOH (98:2 to 90:10) as eluent to yield 5,5-dimethyl-N-(pyrimidin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (90 mol, 27 mg) as a brown solid.

Workup

  1. filtrationAfter filtration
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe crude residue was partitioned between DCM
  4. extractionThe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-336628e580c74cbfb64a46093f3ebddb
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

Loading…