Ammonium Hydroxide → HCID 67050566, compound

HRID 2194776Notes

Reaction equation

HRID 2194776 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][CH2:7][N:8]1[C:13]([C:14](=[O:24])[C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=2)=[C:12]([CH:25]([CH3:27])[CH3:26])[C:11](=[O:28])[NH:10][C:9]1=[O:29])C.[NH4+:31].[OH-]>CO>[C:22]([C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([CH3:21])[CH:18]=1)[C:14]([C:13]1[N:8]([CH2:7][CH:6]=[CH:5][C:4]([NH2:31])=[O:3])[C:9](=[O:29])[NH:10][C:11](=[O:28])[C:12]=1[CH:25]([CH3:26])[CH3:27])=[O:24])#[N:23]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 67050492HCID 67050492, compound

Product 1

HCID 67050566HCID 67050566, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

In a 5 mL microwave reaction tube, 4-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-but-2-enoic acid ethyl ester (69 mg, 0.168 mmol) and 0.5 mL MeOH was added, followed by 0.7 mL NH4OH (30% in water, excess). The reaction mixture was heated in the microwave at 120° C. for 30 minutes. The reaction mixture concentrated down and purified by reverse phase prep HPLC (MeCN/water) to give a white powder (4.2 mg, 6.6%). 1H NMR (300 MHz, CD3OD): δ 8.8 (d, 1H), 7.64 (m, 2H), 7.4-7.28 (m, 2H), 3.19 (dd, 1H), 2.52 (m, 1H), 0.95 (d, 3H), 0.65 (dd, 3H). LC-MS shows 381.0 (M+1).

Workup

  1. concentrationThe reaction mixture concentrated down
  2. custompurified by reverse phase prep HPLC (MeCN/water)

Sources & evidence

ORD record
ord-d3f7da4bccfd4a818e314d0384200748
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

Loading…