Hydrochloric Acid → 2-(2-ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32555Notes

Reaction equation

HRID 32555 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([NH2:16])[C:14]=3[N:15]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[C:3]1[C:23]#[C:24][Si](C)(C)C.O.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[C:23]([C:3]1[N:2]([CH3:1])[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([NH2:16])[C:14]=3[N:15]=2)=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:4]=1)#[CH:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 691941732-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine2×

Product 1

HCID 866016402-(2-ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amineYield 25.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl}[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Intermediate 45) (48 mg) was dissolved/suspended in MeOH (3 mL)/water (1 mL) and potassium carbonate (50 mg) added, then stirred for 90 minutes at ambient temperature. The reaction mixture was neutralised with 2M HCl, concentrated in vacuo, the residue diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extracts were dried (MgSO4), filtered, concentrated in vacuo then purified by flash chromatography on silica eluting with 4% MeOH/DCM to give the title compound as a yellow solid (10 mg, 25%);

Workup

  1. additionadded
  2. concentrationconcentrated in vacuo
  3. additionthe residue diluted with water (10 mL)
  4. extractionextracted with DCM (3×10 mL)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthen purified by flash chromatography on silica eluting with 4% MeOH/DCM

Sources & evidence

ORD record
ord-bf6f14cfc3c84ffd9bd752d7e13150ee
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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