Cyclopropylamine → 6-chloro-N4-cyclopropylpyrimidine-4,5-diamine

HRID 528020Notes

Reaction equation

HRID 528020 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1>C(O)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][CH:10]2[CH2:12][CH2:11]2)[C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 105117206-chloro-N4-cyclopropylpyrimidine-4,5-diamineYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4,6-dichloropyrimidin-5-amine (10 g, 60.9 mmol) and cycloproplyamine (10.44 g, 182.93 mmol, 12.7 mL) in absolute ethanol (100 mL) wee heated at 125° C. in a sealed tube for 4 days. The reaction mixture was then concentrated under reduced pressure to give a yellow solid which was triturated with cold water (200 mL). The resulting slurry was stirred for one hour at room temperature and then filtered. The isolated solid was washed with water (2×25 mL) and dried under reduced pressure to give 11.32 g of the title compound as a pale yellow solid, which was used without any further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give a yellow solid which
  3. customwas triturated with cold water (200 mL)
  4. filtrationfiltered
  5. washThe isolated solid was washed with water (2×25 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5661c384b25847e5ae048516b2e9c23b
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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