4,6-Dichloropyrimidine → HCID 54594436, compound

HRID 1191099Notes

Reaction equation

HRID 1191099 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][CH2:12][CH:9]2[CH2:11][CH2:10]2)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 75646CyclopropanemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 54594436HCID 54594436, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a microwave reaction vessel, slurry 4,6-dichloropyrimidine (540 mg, 3.6 mmol), cyclopropylmethylamine (2800 L, 3.24 mmol), and diisopropylethylamine (1.25 mL, 7.2 mmol) in iso-propanol (3 mL). Irradiate in microwave (300 watts) at 140° C. for 40 min. Cool to room temperature and concentrate in vacuo. Purify by chromatography on silica gel (40 g) eluting with hexane/EtOAc (9:1 to 3:1 over 30 min; 40 mL/min) to obtain the desired intermediate (567 mg, 86%) as an off-white solid. MS (ES+) m/z: 184 (M+H)+.

Workup

  1. customIrradiate in microwave (300 watts) at 140° C. for 40 min
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel (40 g)
  4. washeluting with hexane/EtOAc (9:1 to 3:1 over 30 min; 40 mL/min)

Sources & evidence

ORD record
ord-300afed28ee9431cacaeac404966720a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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