Lithium Hydroxide → HCID 71624964, compound

HRID 1509011Notes

Reaction equation

[O:1]=[S:2]1(=[O:31])[C:11]2[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=3)=[N:9][C:8]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[OH-].[Li+]>>[O:31]=[S:2]1(=[O:1])[C:11]2[C:10]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=3)=[N:9][C:8]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 71625094HCID 71625094, compound

Product 1

HCID 71624964HCID 71624964, compoundYield 86.7%

Procedure

Following general procedure D, ethyl 2-(4-((5,5-dioxido-2-phenyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl)amino)phenyl)acetate (0.80 g, 1.83 mmol) was reacted with lithium hydroxide (0.380 g, 9.15 mmol) to afford the desired product (0.650 g, 86%) as a light yellow solid. MW=409.46. 1H NMR (DMSO-d6, 500 MHz) δ 12.34 (s, 1H), 8.76 (s, 1H), 8.29-8.25 (m, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.59-7.49 (m, 3H), 7.33 (d, J=8.5 Hz, 2H), 3.76-3.72 (m, 2H), 3.60 (s, 2H), 3.08 (t, J=6.5 Hz, 2H), 2.43-2.35 (m, 2H); APCI MS m/z 410 [M+H]+.

Sources & evidence

ORD record: ord-e0b82808ec464e2aa412414039182748
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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