Triphenylphosphine → 5-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyrimidine

HRID 423572Notes

Reaction equation

HRID 423572 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:18][CH:19]([C:21]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][CH:29]([CH2:32]O)[CH2:28][CH2:27]2)[O:23][N:22]=1)[CH3:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:20][CH:19]([C:21]1[N:25]=[C:24]([N:26]2[CH2:27][CH2:28][CH:29]([CH2:32][O:17][C:14]3[CH:15]=[N:16][C:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=4)=[N:12][CH:13]=3)[CH2:30][CH2:31]2)[O:23][N:22]=1)[CH3:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57930076{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanolHCID 666730022-(4-(Methylsulfonyl)phenyl)pyrimidin-5-ol

Product 1

HCID 249934075-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyrimidineYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound (0.145 g, 75%) was prepared as a white solid from 2-[4-(methylsulfonyl)phenyl]-5-pyrimidinol (0.106 g, 0.42 mmol), 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 0.10 g, 0.42 mmol) and Ph3P (0.12 g, 0.42 mmol) in THF (3 mL) followed by diisopropyl azodicarboxylate (92 mg, 94%, 0.42 mmol) in THF (1 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CD3OD): δ 8.61 (s, 2H), 8.58 (d, 2H, J=8.6 Hz), 8.04 (d, 2H, J=8.3 Hz), 4.25-4.10 (m, 2H), 4.12 (d, 2H, J=6.2 Hz), 3.25-3.10 (m, 5H), 2.85 (septet, 1H, J=7.0 Hz), 2.25-2.10 (m, 1H), 2.05-1.90 (m, 2H), 1.55-1.40 (m, 2H), 1.26 (d, 6H, J=7.1 Hz); LRMS (ESI), m/z 458 (M+H).

Sources & evidence

ORD record
ord-c353a102dd8a47ddb147ad1a116f697f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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