Hydrochloric Acid → HCID 11326776, compound

HRID 269800Notes

Reaction equation

HRID 269800 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[C:15]2[N:20]([CH2:21][CH2:22][CH3:23])[C:19](=[O:24])[N:18]([CH2:25][CH2:26][CH3:27])[C:17](=[O:28])[C:16]=2[N+:29]([O-])=O)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl.Cl>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[NH:29][C:16]3[C:17](=[O:28])[N:18]([CH2:25][CH2:26][CH3:27])[C:19](=[O:24])[N:20]([CH2:21][CH2:22][CH3:23])[C:15]=3[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 59833622HCID 59833622, compound

Product 1

HCID 11326776HCID 11326776, compound

Procedure

To a solution of 6-{(1E)-2-[1-benzylpyrazol-4-yl]vinyl}-5-nitro-1,3-dipropyl-1,3-dihydropyrimidine-2,4-dione prepared in Example 18 (0.24 g, 0.57 mmol) in N,N′-dimethyl formamide (4 ml) was added tin (II) chloride (1.07 g, 5.7 mmol). The reaction mixture was heated to 150° for 2 hours. After cooling to room temperature 2N HCl (6 ml) was added and a light brown precipitate formed and was removed by filtration and washed with water (5 ml). The precipitate (0,025 g) was dissolved in DMSO (0.5 ml) and purified using preparative HPLC to yield 6-[1-benzylpyrazol-4-yl]-1,3-dipropyl-1,3-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione, (0.009 g, M+1=392.2)

Workup

  1. temperatureThe reaction mixture was heated to 150° for 2 hours
  2. additionwas added
  3. customa light brown precipitate formed
  4. customwas removed by filtration
  5. washwashed with water (5 ml)
  6. dissolutionThe precipitate (0,025 g) was dissolved in DMSO (0.5 ml)
  7. custompurified

Sources & evidence

ORD record
ord-cc8e47ac91e34f8992d5f219814fb344
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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