Hydrochloric Acid → HCID 59411322, compound

HRID 1366263Notes

Reaction equation

HRID 1366263 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]3[O:20][C:19]([C:21]([O:23]C)=[O:22])=[CH:18][CH:17]=3)[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:11]([CH3:36])=[C:10]2[C:37]([C:39]2[O:40][CH:41]=[CH:42][CH:43]=2)=[O:38])=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].Cl.CO>O1CCCC1.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]3[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=3)[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:11]([CH3:36])=[C:10]2[C:37]([C:39]2[O:40][CH:41]=[CH:42][CH:43]=2)=[O:38])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 59411314HCID 59411314, compound

Product 1

HCID 59411322HCID 59411322, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-{[6-(4-cyanophenyl)-5-(2-furoyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]methyl}-2-furoate (Example 51) (30 mg, 0.51 mmol) in tetrahydrofuran (1.5 ml) is added a solution of lithium hydroxide (2.4 mg, 0.10 mmol) in water (1.5 ml). The reaction is stirred at room temperature overnight (16 h), then acidified with 1 N hydrochloric acid. A precipitate is obtained. Methanol (7 ml) is added, and the crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 30:70→90:10).

Workup

  1. customA precipitate is obtained
  2. customthe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/0.1% aq. formic acid 30:70→90:10)

Sources & evidence

ORD record
ord-0b6729f65ee7480c8c616bc49380d0d5
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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