Pyridine → HCID 10049720, compound

HRID 32645Notes

Reaction equation

HRID 32645 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]=[CH:21][N:22]([CH3:34])[C:23]=2[C:24]2[S:33][C:27]3[N:28]=[CH:29][N:30]=[C:31]([NH2:32])[C:26]=3[CH:25]=2)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>C1COCC1>[NH2:32][C:31]1[C:26]2[CH:25]=[C:24]([C:23]3[N:22]([CH3:34])[CH:21]=[N:20][C:19]=3[C:15]3[CH:14]=[C:13]([NH:12][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:18]=[CH:17][CH:16]=3)[S:33][C:27]=2[N:28]=[CH:29][N:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 690543996-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine2×

Product 1

HCID 10049720HCID 10049720, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzylchloroformate (0.027 mL) was added to a solution of 6-[4-(3-aminophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Intermediate 110) (40 mg) and pyridine (0.02 mL) in THF (7 mL). The mixture was stirred under an inert atmosphere for 1 hour, then quenched with H2O (10 mL) and extracted EtOAc (3×10 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with CH2Cl2:MeOH (0-10%) gave the title compound as a gum (16 mg, 28%);

Workup

  1. customquenched with H2O (10 mL)
  2. extractionextracted EtOAc (3×10 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with CH2Cl2

Sources & evidence

ORD record
ord-ae6d26d1786a42c2b374378e0d771643
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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