Hydrochloric Acid → HCID 59239069, compound

HRID 1698048Notes

Reaction equation

HRID 1698048 reaction equation
[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:15]3[CH2:21][CH2:20][N:19]([C:22]4[N:27]=[C:26]([C:28]([O:30]C)=[O:29])[CH:25]=[C:24]([CH3:32])[N:23]=4)[CH2:18][C:16]=3[N:17]=2)=[CH:8][CH:7]=1)[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[C:15]3[CH2:21][CH2:20][N:19]([C:22]4[N:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[C:24]([CH3:32])[N:23]=4)[CH2:18][C:16]=3[N:17]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59239507HCID 59239507, compound

Product 1

HCID 59239069HCID 59239069, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

methyl 2-(2-(4-(3-ethylureido)-phenyl)-4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-6-methylpyrimidine-4-carboxylate (yc) (0.25 mmol) in a mixed solvent of NaOH (10%, 5 mL) and MeOH (5 mL) were stirred at room temperature overnight. The mixture was neutralized with diluted HCl to pH=6 and extracted with ethyl acetate thrice. The combined organic phases were dried over Na2SO4 and concentrated to give 50.6 mg of 2-(2-(4-(3-ethyl-ureido)phenyl)-4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-6-methylpyrimidine-4-carboxylic acid (yd): 1H NMR (D6-DMSO, 400 MHz) δ 8.18 (d, J=8.8, 2H), 7.51 (d, J=8.0, 2H), 6.91 (s, 1H), 4.84 (s, 2H), 3.96 (m, 2H), 3.69 (s, 4H), 3.41 (s, 4H), 3.09 (t, J=7.2, 2H), 2.67 (s, 2H), 2.32 (s, 3H), 1.04 (t, J=7.2, 2H); LC-MS: m/z=+519 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate thrice
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59888fb7afe14f15aefbcd7f9413189c
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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