Potassium ethanethioate → HCID 178476933, compound

HRID 2197469Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[C:25](Br)=[N:24][C:23]3[C:18]2=[N:19][C:20]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[N:21][C:22]=3[NH2:27])[CH:11]=1)(=[O:8])[O:5]CC)[CH3:2].C([O-])(=[S:35])C.[K+]>CN(C=O)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[C:25]([SH:35])=[N:24][C:23]3[C:18]2=[N:19][C:20]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[N:21][C:22]=3[NH2:27])[CH:11]=1)(=[O:8])[OH:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3-(6-Amino-8-bromo-2-(2-methoxy-ethoxy)-purin-9-ylmethyl)-benzyl)-phosphonic acid diethyl ester (50) (180 mg, 0.34 mmol) in DMF (2 ml) was added potassium thioacetate (778 mg, 6.8 mmol). The reaction mixture stirred at 100° C. for 24 h. After cooling to rt, the reaction mixture was filtered and purified by reversed phase prep-HPLC using a linear gradient of acetronitrile in water from 5% to 95%. 1H NMR (DMSO, 300 MHz): (1.08 (t, 3H), (3.00 (d, 2H), (3.25 (s, 3H), (3.58 (t, 2H), (3.77-3.84 (m, 2H), (4.29 (t, 2H), (5.23 (s, 2H), (6.87 (bs, 2H), (7.16-7.28 (m, 4H); 31P NMR (DMSO, 300 MHz): (23.20; MS: 454.1 (M+H)+, 452.0 (M−1).

Workup

temperatureAfter cooling to rt
filtrationthe reaction mixture was filtered
custompurified by reversed phase prep-HPLC

Sources & evidence

ORD record: ord-1c6aea96be9c45959384746d83f4dffc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338593B2

Reaction notes

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