Lithium Hydroxide → HCID 59200029, compound

HRID 2381976Notes

Reaction equation

HRID 2381976 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1[C:7](=[O:28])[N:8]([NH:13][C:14]([C:16]2[CH:17]=[N:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20][CH:21]=2)=[O:15])[C:9](=[O:12])[NH:10][CH:11]=1.[Li+].[OH-]>CO.O.C1COCC1>[O:12]=[C:9]1[N:8]([NH:13][C:14]([C:16]2[CH:21]=[N:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][CH:17]=2)=[O:15])[C:7](=[O:28])[C:6]([CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:11][NH:10]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59199989HCID 59199989, compound

Product 1

HCID 59200029HCID 59200029, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-{2,4-Dioxo-3-[(2-pheyl-pyrimidine-5-carbonyl)-amino]-1,2,3,4-tetrahydro-pyrimidin-5-yl}-propionic acid methyl ester (0.22 mol) is hydrolyzed by LiOH (0.88 mol) in MeOH/water/THF (1:1:1) at rt overnight. MeOH and THF are evaporated in vacuo. The residue is acidified by 5% aqueous HCl. The resulting precipitate is collected and dried to afford 3-{2,4-dioxo-3-[(2-pheyl-pyrimidine-5-carbonyl)-amino]-1,2,3,4-tetrahydro-pyrimidin-5-yl}-propionic acid (40 mg, 48%). MS: 383 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.68-2.77 (m, 2H), 2.98-2.90 (m, 2H), 5.49 (s. N—H), 7.48-7.60 (m, 3H), 8.41-8.56 (m, 2H), 9.32 (s, 2H).

Workup

  1. customMeOH and THF are evaporated in vacuo
  2. customThe resulting precipitate is collected
  3. customdried

Sources & evidence

ORD record
ord-ed6fa00063244d5f857b380c74602249
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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