Cyclopropylamine → HCID 86694157, compound

HRID 707289Notes

Reaction equation

HRID 707289 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1>>[Br:9][C:5]1[N:6]=[C:7]([NH:13][CH:10]2[CH2:12][CH2:11]2)[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 69828Cyclopropylamine2×HCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 86694157HCID 86694157, compound

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with 2-amino-3,5-dibromopyrazine (1.00 g, 3.95 mmol) and cyclopropylamine (1.40 ml, 19.96 mmol). The reaction mixture was sealed under argon and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. Additional cyclopropylamine (1.0 mL) was added and the reaction was heated at 120° C. for 30 min in the microwave. Excess cyclopropylamine was removed in vacuo and the residue was dissolved in MeOH and evaporated onto silica gel and purified by flash chromatography (Isco (40 gram)) eluting with EtOAc:hexanes (0:1→1:2) to give 740 mg (82%) of a golden-brown tar. ESI MS 228.9 [M+1].

Workup

  1. customA glass microwave reaction vessel
  2. customThe reaction mixture was sealed under argon
  3. temperaturethe reaction was heated at 120° C. for 30 min in the microwave
  4. customExcess cyclopropylamine was removed in vacuo
  5. dissolutionthe residue was dissolved in MeOH
  6. customevaporated onto silica gel
  7. custompurified by flash chromatography (Isco (40 gram))
  8. washeluting with EtOAc:hexanes (0:1→1:2)
  9. customto give 740 mg (82%) of a golden-brown tar

Sources & evidence

ORD record
ord-81800ddac1254122b504284c7e43d76e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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