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

HRID 539248Notes

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)(12.00 g, 40.63 mmol) in NMP (97.45 g) was added triethyamine (6.17 g, 90.65 mmol) and the mixture was cooled to 5° C. Thereto was dropped methanesulfonyl chloride (6.05 g, 52.82 mmol) and the mixture was stirred at 5° C. for 30 minutes, followed by adding a water (244.00 g). After stirring for 1 hour, the resulting crystal was filtered to give the subject compound (30.34 as a crude product). Purity: 98.39% (HPLC)

Workup

stirringAfter stirring for 1 hour
filtrationthe resulting crystal was filtered

Sources & evidence

ORD record: ord-dd7769132919416ebcd6329beb803a40
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865896B2

Reaction notes

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