Sulfuric Acid → HCID 71667335, compound

HRID 1481255Notes

Reaction equation

HRID 1481255 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[C:11]([NH2:21])=[CH:10][N:9]=2)[CH:4]=[N:3]1.S(=O)(=O)(O)O.[N:27]([O-])=O.[Na+]>O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[N:21]=[N:27][N:14]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[C:12]=3[N:13]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 89720126HCID 89720126, compound

Product 1

HCID 71667335HCID 71667335, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 80 mg (0.28 mmol) N2,N4-bis-(1-methyl-1H-pyrazol-4-yl)-pyrimidine-2,4,5-triamine in 23 ml water is treated with 4 ml concentrated sulfuric acid and then with 39 mg (0.56 mmol) sodium nitrite. The reaction mixture is stirred for 90 minutes at room temperature. The reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent giving “A21” as off-white crystals; HPLC/MS (A) 1.42 min, [M+H] 297;

Workup

  1. customThe reaction mixture is partitioned between water and dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent
  5. customgiving “A21” as off-white crystals

Sources & evidence

ORD record
ord-2de60350c7f84f2a84f5a8c518db8d7f
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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