Isopropylamine → 7-bromo-N-isopropylthieno[3,2-d]pyrimidin-4-amine

HRID 1518349Notes

Reaction equation

HRID 1518349 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.[CH3:12][CH:13]([NH2:15])[CH3:14]>C(O)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH:15][CH:13]([CH3:14])[CH3:12])[C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidine

Product 1

HCID 594476427-bromo-N-isopropylthieno[3,2-d]pyrimidin-4-amineYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 65A (0.125 g, 0.5 mmol), and propan-2-amine (0.148 g, 2.5 mmol) in ethanol (10 mL) was heated under reflux for 15 hours. The solvent was removed, and the residue was purified by flash column chromatography on silica gel eluting with 1:1 EtOAc/hexanes to give 0.13 g of the title compound: 1H NMR (DMSO-d6): δ 8.50 (s, 1H), 8.28 (s, 1H), 7.87 (d, J=7.46 Hz, 1H), 4.40-4.51 (m, 1H), 1.23 (d, J=6.78 Hz, 6H). ESI (+)/MS: 273 (M−H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customThe solvent was removed
  4. customthe residue was purified by flash column chromatography on silica gel eluting with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-aa75aeb3fff744859c76736ba0694afb
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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