7-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine → 7-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine

HRID 1485486Notes

Reaction equation

HRID 1485486 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.C(O)(C)C.[NH3:17]>>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10]([NH2:17])[C:5]=2[S:4][CH:3]=1

Participants

3

Reactant 2

HCID 183264227-Bromo-2,4-dichlorothieno[3,2-d]pyrimidineHCID 183319422-Propanol, reaction products with ammonia, distn. residues

Product 1

HCID 866756507-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amineYield 75%

Conditions

Temperature
80 °C

Procedure

7-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine (3.0 g, 10.64 mmol) was added to a sealed reactor and 2.0 N ammonia isopropanol (26.6 mL, 53.2 mmol) was added thereto. The reaction mixture was stirred at 80° C. for 5 hours and then cooled to room temperature. The reaction mixture was added to ice water (100 mL). Thus prepared solid was filtered and dried by blowing nitrogen gas. The resultant target compound (2.1 g, 75% yield) was used in the following reaction without purification.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThus prepared solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-a6b9a5b1fcff43afa9f3bf05afcfca12
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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