Propylamine → HCID 178456834, compound

HRID 928238Notes

Reaction equation

HRID 928238 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7](SC)=[N:8][CH:9]=2)[NH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=O.[CH2:24]([NH2:27])[CH2:25][CH3:26]>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH:27][CH2:24][CH2:25][CH3:26])=[N:8][CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 70297m-Chloroperbenzoic acidHCID 178503373HCID 178503373, compound

Product 1

HCID 178456834HCID 178456834, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 3-bromo-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (0.49 g, 2.0 mmol) in THF (5 mL) was added meta-chloroperoxybenzoic acid (0.52 g, 99%, 3 mmol) at room temperature. The white mixture was stirred for 2 h and n-propylamine (0.82 mL, 10 mmol) was added at 0° C. The resulting solution was heated at 40° C. for 12 h. After removal of the solvent, MeOH was added and the mixture was filtered. The white solid was washed with MeOH (3×) and dried to provide 3-bromo-N-propyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (0.45 g, 88%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.19 (bs, 1H), 8.63 (s, 1H), 7.69 (bs, 1H), 3.29-3.17 (m, 2H), 1.61-1.49 (m, 2H), 0.88 (t, J=7.4 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) δ 161.61, 156.98, 152.71, 120.06, 106.66, 42.68, 21.72, 11.47; MS m/z 256.1 [M+1].

Workup

  1. customAfter removal of the solvent, MeOH
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. washThe white solid was washed with MeOH (3×)
  5. customdried

Sources & evidence

ORD record
ord-ad8da6871a5d4a6bbf55dc4df17f3ff6
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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