Ammonia → 7-Bromothieno[3,2-d]pyrimidin-4-amine

HRID 1464976Notes

Reaction equation

HRID 1464976 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.[NH3:12]>C(O)(C)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:12])[C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidine

Product 1

HCID 673608657-Bromothieno[3,2-d]pyrimidin-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

7-Bromo-4-chlorothieno[3,2-d]pyrimidine (5 g, 20.17 mmol) obtained in Step 3 of Preparation Example 1 and 2.0M NH3 dissolved in isopropanol solution (50 mL) were added to a sealed reaction vessel and stirred at 100° C. for 12 hours. The reaction mixture was cooled to room temperature and filtered to obtain a solid. The solid was washed with water and dried with N2 gas to obtain the title compound (3.8 g, 83%) without further purification.

Workup

  1. additionwere added to a sealed reaction vessel
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto obtain a solid
  5. washThe solid was washed with water
  6. dry with materialdried with N2 gas

Sources & evidence

ORD record
ord-ec173c7db495431682d8f1447eedaf48
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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