Sodium Hydroxide → HCID 15485645, compound

HRID 367267Notes

Reaction equation

HRID 367267 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[N:4]([CH3:14])[C:5](=[O:13])[N:6]([CH2:9][CH2:10][CH2:11][CH3:12])[C:7]=1[CH3:8].[N:16]([O-])=O.[Na+].[OH-].[Na+]>O.Cl>[CH2:9]([N:6]1[C:7]2[CH:8]=[N:16][NH:1][C:2]=2[C:3](=[O:15])[N:4]([CH3:14])[C:5]1=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15485644HCID 15485644, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15485645HCID 15485645, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To 1.03 g (4.88 mmol) of 5-amino-1-butyl-3,6-dimethyl-1H-pyrimidine-2,4-dione in 20 mL H2O and 5 mL conc HCl at 0° C. was added a solution of 320 mg (4.64 mmol) of NaNO2 and 3 mL H2O in drops such that the internal reaction temperature does not exceed 5° C. (10 min). After stirring for an additional 10 min, the resulting slurry was added in drops to a 0° C. solution of 20% aq. NaOH. After addition is complete, the resulting solution is stirred at 23° C. for 20 min, neutralized to pH ~7 with dilute aq. HCl, poured into 200 mL of pH 7 buffer, and extracted with 2×150 mL EtOAc. The combined organics were dried over Na2SO4, filtered and evaporated to an orange solid. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (20/1 to 4/1), gave 617 mg (2.78 mmol, a 57% yield) of the title compound as an off-white solid. mp: 160-162° C.; 1H NMR (300 MHz, CDCl3): δ 0.98 (t, J=7.4 Hz, 3H), 1.44 (hex, J=7.3 Hz, 2H), 1.71-1.80 (m, 2H), 3.47 (s, 3H), 3.95 (t, J=7.4 Hz, 2H), 7.56 (s, 1H); IR (KBr, cm-1): 3142w, 2953w, 2932w, 1708s, 1649s, 1610s, 1296w; MS (ES) m/z (relative intensity): 223 (M+ +H, 100). Anal. Calcd for C10H14N4O2 : C, 54.04; H, 6.35; N, 25.21. Found: C, 52.50; H, 6.23; N, 22.64.

Workup

  1. customdoes not exceed 5° C.
  2. custom(10 min)
  3. additionAfter addition
  4. stirringthe resulting solution is stirred at 23° C. for 20 min
  5. additionpoured into 200 mL of pH 7 buffer
  6. extractionextracted with 2×150 mL EtOAc
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to an orange solid
  10. washFlash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (20/1 to 4/1)
  11. customgave 617 mg (2.78 mmol

Sources & evidence

ORD record
ord-ef9af0755924442e96fd7cf8496dfd74
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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