Ammonia → HCID 59465189, compound

HRID 1714845Notes

Reaction equation

HRID 1714845 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:14][C:15]2[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:25]([O-:27])=[O:26])=[C:4]([CH3:28])[N:3]=1.[NH3:29]>C1COCC1>[NH2:29][C:2]1[N:7]=[C:6]([N:8]([CH2:14][C:15]2[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([N+:25]([O-:27])=[O:26])=[C:4]([CH3:28])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86622375HCID 86622375, compound2×

Product 1

HCID 59465189HCID 59465189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[(2-chloro-6-methyl-5-nitro-pyrimidin-4-yl)-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl]amino]acetate (Intermediate 28)(465 mg, 1.13 mmol) was stirred in THF (50 mL) and ammonia (28% in water, 10 mL) was added and the mixture stirred at room temperature overnight. The mixtures were concentrated in vacuo and water (200 mL) was added and extracted with DCM (3×100 mL) and concentration in vacuo yielded Intermediate 27 an orange solid (437 mg, 99%); 1H NMR spectrum (400 MHz, DMSO-d6) δ 2.21 (9H, m), 3.63 (3H, d), 3.73 (3H, s), 4.39 (2H, d), 4.98 (2H, d), 7.90 (2H, s), 8.14 (1H, s); Mass spectrum: (M+H)+ 391.

Workup

  1. concentrationThe mixtures were concentrated in vacuo and water (200 mL)
  2. additionwas added
  3. extractionextracted with DCM (3×100 mL) and concentration in vacuo

Sources & evidence

ORD record
ord-5e4e7e01519d491aab49e2d698883a9e
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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