Water → 3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl methanesulfonate

HRID 339941Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:20][CH3:21])[N:6]2[CH2:16][CH2:17][CH2:18][OH:19].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>CN1C(=O)CCC1>[CH3:29][S:30]([O:19][CH2:18][CH2:17][CH2:16][N:6]1[C:5]([O:20][CH3:21])=[N:4][C:3]2[C:7]1=[N:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:10][C:2]=2[NH2:1])(=[O:32])=[O:31]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 3-(6-amino-2-butoxy-8-methoxy-9H-purin-9-yl)propan-1-ol (18.0 g, 61.0 mmol) in NMP (146 g) was added triethylamine (9.3 g, 91.4 mmol) and the mixture stirred at 5° C. Methanesulfonylchloride (9.1 g, 79.2 mmol) was added dropwise to the solution and stirred at 5° C. for 30 min. Water (144 g) was added, the mixture stirred for 1 hr and the suspension filtered to give the subtitle compound as water wet cake, which was directly used in the next reaction. Yield 42.4 g as a crude product.

Workup

stirringstirred at 5° C. for 30 min
stirringthe mixture stirred for 1 hr
filtrationthe suspension filtered

Sources & evidence

ORD record: ord-b7fe6a1530eb4c838810cdaa04857062
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895570B2

Reaction notes

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