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Water → N-benzyl-7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine

HRID 1485502
Notes
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Reaction equation

HRID 1485502 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.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[CH2:13]([NH:20][C:10]1[C:5]2[S:4][CH:3]=[C:2]([Br:1])[C:6]=2[N:7]=[C:8]([Cl:12])[N:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 183264227-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 86675658N-benzyl-7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-amineYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

7-Bromo-2,4-dichlorothieno[3,2-d]pyrimidine (500 mg, 1.77 mmol) was dissolved in anhydrous tetrahydrofuran (8 mL) and stirred at 60° C. for 2 hours after adding benzylamine (0.58 mL, 5.32 mmol). The reaction mixture was cooled to room temperature and added to water (30 mL). Thus prepared solid was filtered and dried with nitrogen gas. The resultant target compound (580 mg, 92% yield) was used in the following reaction without purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThus prepared solid was filtered
  3. customdried with nitrogen gas

Sources & evidence

ORD record
ord-8417bf218e0248379ddd660e09c0c12f
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422307B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes