Lithium hydroxide, monohydrate → HCID 22125078, compound

HRID 1858293Notes

Reaction equation

[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([CH2:26][C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=3)[C:30]([O:32]C)=[O:31])[C:15](=[O:25])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([CH2:26][C:27]3[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=3)[C:30]([OH:32])=[O:31])[C:15](=[O:25])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 90 mg (0.17 mmol) of methyl 3-[[7-anilino-3-(2-bromophenyl)-1,2,3,4-tetrahydro-2-oxopyrimido[4,5-d]pyrimidin-1-yl]methyl]benzoate in tetrahydrofuran/methanol/water (6 ml:6 ml:1.5 ml) was treated with 27 mg (1.125 mmol) of lithium hydroxide monohydrate then heated at 60° C. for 3 hours under a nitrogen atmosphere. The solvent was evaporated and the residue partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml). The ethyl acetate layer was separated, washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated to give 30 mg (35%) of 3-[[7-anilino-3-(2-bromophenyl)-1,2,3,4-tetrahydro-2-oxopyrimido[4,5-d]pyrimidin-1-yl]methyl]benzoic acid as a pale yellow solid of melting point 180-183° C. [Mass spectrum (ESI) MH+ =530].

Workup

customThe solvent was evaporated
customthe residue partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml)
customThe ethyl acetate layer was separated
washwashed with saturated aqueous sodium bicarbonate (10 ml)
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-4175680d9acd477ca88aecf1ffa7a4b9
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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