Ammonia → HCID 10385729, compound

HRID 32549Notes

Reaction equation

HRID 32549 reaction equation
CO[C:3]1[C:4]2[N:11]=[C:10]([C:12]3[N:16]([CH3:17])[C:15]([C:18]4[CH:22]=[CH:21][S:20][CH:19]=4)=[N:14][C:13]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.[NH3:29]>O1CCOCC1>[CH3:17][N:16]1[C:12]([C:10]2[S:9][C:5]3[N:6]=[CH:7][N:8]=[C:3]([NH2:29])[C:4]=3[N:11]=2)=[C:13]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:14]=[C:15]1[C:18]1[CH:22]=[CH:21][S:20][CH:19]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 691963357-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine2×

Product 1

HCID 10385729HCID 10385729, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

7-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine (Intermediate 44) (26 mg) was dissolved in 0.5M NH3 in 1,4-dioxane (3 mL)/concentrated aqueous NH3 (0.6 mL), sealed and heated under microwave conditions (CEM explorer, 150° C., 150 W) for 1 hour. After which the reaction mixture was concentrated in vacuo, dissolved in EtOAc (20 mL), washed: with 2M NaOH (2×10 mL) then brine (1×15 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 4% MeOH/DCM gave the title compound as an off-white solid (17 mg, 68%);

Workup

  1. customsealed
  2. concentrationAfter which the reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in EtOAc (20 mL)
  4. washwashed
  5. dry with materialwith 2M NaOH (2×10 mL) then brine (1×15 mL), dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica eluting with 4% MeOH/DCM

Sources & evidence

ORD record
ord-0f57808aac8a486bb047d3836ae103b0
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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