Sodium methanethiolate → (S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-hydroxyphenyl)acetic acid

HRID 1617243Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:12][CH2:13][CH3:14])[CH2:10][OH:11])[C:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=2[O:26]C)=[C:4]([CH3:28])[N:3]=1.C[S-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:12][CH2:13][CH3:14])[CH2:10][OH:11])[C:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=2[OH:26])=[C:4]([CH3:28])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the product from example 30 step (v) (250 mg) in DMF (20 ml), sodium thiomethoxide (180 mg) was added and stirred at 100° C. for 16 h. The solvents were evaporated, and crude product purified by RPHPLC to give the subtitle compound as a colourless gum, 120 mg. LC/MS m/z 375 APCI+

Workup

customThe solvents were evaporated
customcrude product purified by RPHPLC

Sources & evidence

ORD record: ord-a2568ce4b8e345a1825d9a015fe0664c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765939B2

Reaction notes

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