Diisopropylethylamine → HCID 60124244, compound

HRID 2206620Notes

Reaction equation

HRID 2206620 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:10]1([C@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[C:3]([NH:18][C@@H:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:17])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 60124244HCID 60124244, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (5 g, 22 mmol) and (R)-1-phenylethanamine (2.7 g, 22 mmol) in ethanol (50 mL) was added N,N-diisopropylethylamine (4.3 g, 33 mmol). The reaction solution was stirred at room temperature for 12 hours. The resultant mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1) to give (R)-5-bromo-2-chloro-N-(1-phenylethyl)pyrimidin-4-amine as a white solid (5 g, 74%). LRMS (M+H) m/z: calcd 310.98. found 310. 1H NMR (300 MHz, CDCl3): δ 8.10 (s, 1H), 7.41-7.25 (m, 5H), 5.73 (d, J=6.9 Hz, 1H), 5.39-5.34 (m, 1H), 1.61 (d, J=6.6 Hz, 3H).

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-478d98dcba9242398e575ea47cae3a60
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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