Triphenylphosphine → 1,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423568Notes

Reaction equation

HRID 423568 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28]O)[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11]([O:14][CH2:28][CH:25]3[CH2:26][CH2:27][N:22]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:23][CH2:24]3)=[CH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6199082-(4-Bromophenyl)pyrimidin-5-olHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 666731161,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate was prepared (0.387 g, 76%) as a white solid from 2-(4-bromophenyl)-pyrimidine-5-ol (0.30 g, 1.19 mmol), N-Boc-4-piperidinemethanol (0.27 g, 1.19 mmol) and Ph3P (0.32 g, 1.19 mmol) in THF (8 mL) followed by diisopropyl azodicarboxylate (0.26 g, 94%, 1.19 mmol) in THF (3 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 8.44 (s, 2H), 8.22 (d, 2H, J=8.3 Hz), 7.59 (d, 2H, J=8.3 Hz), 4.25-4.10 (m, 2H), 3.94 (d, 2H, J=6.1 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 448/450 (M+H).

Sources & evidence

ORD record
ord-131a37b696e642708fd1ae02d3e1e94b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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