Triphenylphosphine → HCID 18431005, compound

HRID 1278583Notes

Reaction equation

HRID 1278583 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:10]=[N:11][C:12]([C:15]2([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)=O)([CH3:5])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:21]([N:18]1[CH2:17][CH2:16][C:15]([C:12]2[N:13]=[CH:14][C:9]([C:7]3[O:1][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=3)=[CH:10][N:11]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86758494HCID 86758494, compound

Product 1

HCID 18431005HCID 18431005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (350 mg, 0.745 mmol) and triphenylphosphine (290 mg, 1.11 mmol) in tetrahydrofuran (10 mL) at 0° C. was added diethylazodicarboxylate (0.174 mL, 1.11 mmol). The reaction slowly warmed to room temperature and stirred for 3 hours. The crude mixture was concentrated under reduce pressure and purified by flash chromatography with 2% MeOH/CH2Cl2 to afford 175 mg (%) of the desired product. 1HNMR (400 MHz, CDCl3) δ 9.12 (s, 2H), 7.33-7.26 (comp, 5H), 7.15 (t, 1H), 6.95-6.91 (comp, 2H), 6.68-4.65 (comp, 1H), 4.09 (s, 2H), 3.72 (s, 3H), 3.42 (br s, 2), 3.04 (br s, 2H), 2.83 (br s, 2H), 2.37 (br s, 2H), 2.03 (br s, 2H), 1.36 (s, 6H); MS (M+1) 457.1

Workup

  1. customThe reaction
  2. concentrationThe crude mixture was concentrated
  3. custompurified by flash chromatography with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c4f028166f154235b1a4bdd3e2dc8077
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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