Triethylamine → Trimethylsilylethyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamate

HRID 1868464Notes

Reaction equation

HRID 1868464 reaction equation
[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([CH:23]=[C:24](C(O)=O)[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1.[Si:47]([CH2:51][CH2:52][OH:53])([CH3:50])([CH3:49])[CH3:48].CC[N:56]([CH2:59]C)CC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([CH:23]=[C:24]([NH:56][C:59]([O:53][CH2:52][CH2:51][Si:47]([CH3:50])([CH3:49])[CH3:48])=[O:37])[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 670215506-((Tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

Product 1

HCID 67021519Trimethylsilylethyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamateYield 25.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (Example 58, Step 2, 45 mg, 0.1 mmol) in PhCH3 (3 mL) was added DPPA (43 μL, 0.2 mmol), TMSCH2CH2OH (71 μL, 0.5 mmol) and Et3N (31 μL, 0.22 mmol). The reaction was heated to 65° C. for 16 h and was concentrated under reduced pressure. The resulting residue was diluted with EtOAc and extracted with satd aq NH4Cl, NaHCO3 and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded trimethylsilylethyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carbamate (14 mg, 25%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc
  3. extractionextracted with satd aq NH4Cl, NaHCO3 and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-aec46ade0af0420bb076dc5d511a2c0f
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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