Sodium → HCID 44274811, compound

HRID 2375428Notes

Reaction equation

HRID 2375428 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH3:21])[N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=3)[C:10]([CH3:11])=[C:6]2[C:5]([CH3:22])=[N:4][N:3]=1.[CH3:23][O-:24].[Na+].[Na]>CO>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[C:10]([CH3:11])=[C:6]3[C:7]([C:2]([O:24][CH3:23])=[N:3][N:4]=[C:5]3[CH3:22])=[C:8]2[CH3:21])=[CH:13][CH:14]=1)[CH3:20]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 86606406HCID 86606406, compound

Product 1

HCID 44274811HCID 44274811, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 1-chloro-6-(4-ethoxyphenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine (EXAMPLE 85) (100 mg, 0.32 mmol) and MeOH (5 mL) was treated with a solution of NaOMe (freshly prepared from MeOH (5 mL) and sodium metal (22 mg, 0.96 mmol)). The resulting mixture was placed in a resealable reaction vessel and heated at 100° C. for 12 h. The reaction was allowed to cool to rt, and poured into ice water (100 mL) to give 6-(4-ethoxyphenyl)-1-methoxy-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine: 1H NMR (CDCl3, 500 MHz) δ 7.11-7.25 (m, 4H), 4.16 (q, 2H), 2.71 (s, 3H), 2.40 (s, 3H), 2.38 (s, 3H), 1.43-1.46 (t, 3H); MS (ESI) 312 (M+H)+.

Workup

  1. customThe resulting mixture was placed in a resealable reaction vessel
  2. temperatureto cool to rt

Sources & evidence

ORD record
ord-2ff0414152e6432c9b8b49c0ef53bd4b
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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