Methanesulfonyl chloride → Methanesulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-ylmethyl ester

HRID 480175Notes

Reaction equation

HRID 480175 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]3[NH:19][C:18]4[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15](=[O:24])[N:14]([CH2:25][CH2:26][CH3:27])[C:13]=4[N:12]=3)([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[O:24]=[C:15]1[N:14]([CH2:25][CH2:26][CH3:27])[C:13]2[N:12]=[C:11]([C:6]34[CH2:7][CH2:8][C:3]([CH2:2][O:1][S:29]([CH3:28])(=[O:31])=[O:30])([CH2:10][CH2:9]3)[CH2:4][CH2:5]4)[NH:19][C:18]=2[C:17](=[O:20])[N:16]1[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 119956518-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

Product 1

HCID 86591751Methanesulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a mixture of 8-(4-hydroxymethylbicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydropurine-2,6-dione (X, Example 86) in pyridine at 0° is added methanesulfonyl chloride (1.2 equivalents) in pyridine. The mixture is stirred at 0° until complete conversion is achieved and then the solvent removed under reduced pressure.

Workup

  1. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0e1510ad8d0d40e787b79fd84e1e072b
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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