N,N'-Dimethylethylenediamine → tert-Butyl {3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}carbamate

HRID 32633Notes

Reaction equation

HRID 32633 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][N:11]([CH3:23])[C:12]=2[C:13]2[S:22][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:21])[C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:24](=[O:31])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[NH2:25].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[NH2:21][C:20]1[C:15]2[CH:14]=[C:13]([C:12]3[N:11]([CH3:23])[CH:10]=[N:9][C:8]=3[C:4]3[CH:3]=[C:2]([NH:25][C:24](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:7]=[CH:6][CH:5]=3)[S:22][C:16]=2[N:17]=[CH:18][N:19]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 103206356-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 86760727tert-Butyl {3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}carbamateYield 9.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-[4-(3-Iodophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Example 49) (43 mg) was stirred with tert-butyl carbamate (24 mg), N,N′-dimethylethylenediamine (9 mg), copper(I) iodide (10 mg), and potassium phosphate (42 mg) in 1,4-dioxane (2 mL), degassed, and heated under an inert atmosphere at 100° C. for 24 hours. The mixture was partitioned between EtOAc and dilute aqueous NH3. The organic phase was dried and evaporated. The residue was purified by flash chromatography on silica using a gradient of 0-100% EtOAc in DCM then 0-20% MeOH in DCM as eluent. Fractions were evaporated to give the title compound as a gum (4 mg, 9%);

Workup

  1. customdegassed
  2. customThe mixture was partitioned between EtOAc and dilute aqueous NH3
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica using a gradient of 0-100% EtOAc in DCM
  6. customFractions were evaporated

Sources & evidence

ORD record
ord-91338da205db4600923c3a2fc907939b
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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