Azidotrimethylsilane → HCID 178444677, compound

HRID 1278581Notes

Reaction equation

HRID 1278581 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2].[N:34]([Si](C)(C)C)=[N+:35]=[N-:36]>C1(C)C=CC=CC=1>[CH2:32]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:36][N:35]=[N:34][N:31]=4)[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:33]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 70157614HCID 70157614, compound

Product 1

HCID 178444677HCID 178444677, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 2-[4-(3-cyano-phenyl)-1-(2-methyl-pentyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid diethylamide (45 mg, 0.11 mmol) in 4 mL toluene at room temperature was added Bu2SnO (12 mg, 0.05 mmol) and azidotrimethylsilane (0.09 mL, 0.66 mmol). The reaction mixture was heated to 100° C. for 28 hours and cooled to room temperature. The reaction was quenched with water, neutralized with NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The resulting crude material was purified by flash chromatography with 5% MeOH/CH2Cl2 to afford 25 mg (51%) of the desired tetrazole. 1HNMR (400 MHz, CDCl3) δ 8.70 (s, 2H), 8.15 (s, 1H), 7.94 (d, 1H), 7.25-7.13 (comp, 2H), 3.53-3.51 (comp, 4H), 3.25-3.22 (comp, 4H), 2.70 (br s, 6H), 1.93 (br s, 1H), 1.40-1.12 (comp, 10H), 1.01 (d, 3H), 0.81 (t, 3H); MS (M+1) 491.4.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe resulting crude material was purified by flash chromatography with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-0924920bcf6648d586fa35f78507be90
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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