Sodium Hydroxide → 1,1-Dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423569Notes

Reaction equation

HRID 423569 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Na+].[CH3:30][S:31]([O-:33])=[O:32].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O>[CH3:30][S:31]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 666731161,1-Dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate

Product 1

HCID 591778161,1-Dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylateYield 31.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound (0.12 g, 31%) was prepared as a white solid from 1,1-dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate (0.385 g, 0.86 mmol), methanesulfinic acid sodium salt (0.16 g, 80%, 1.29 mmol), L-proline (20 mg, 0.17 mmol), Cul (17 mg, 0.09 mmol) and NaOH (7 mg, 0.17 mmol) in DMSO (5 mL) in a manner similar to Example 76, Step 3. 1H NMR (400 MHz, CD3OD): δ 8.60 (s, 2H), 8.57 (d, 2H, J=8.5 Hz), 8.03 (d, 2H, J=8.6 Hz), 4.20-4.10 (m, 2H), 4.08 (d, 2H, J=6.1 Hz), 3.15 (s, 3H), 2.90-2.75 (m, 2H), 2.15-2.00 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.40-1.25 (m, 2H); LRMS (ESI), m/z 448 (M+H).

Sources & evidence

ORD record
ord-04cde0258cb14cccb00401b9a5d9766b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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