4-Methoxybenzylamine → HCID 22143697, compound

HRID 1824724Notes

Reaction equation

HRID 1824724 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>C(O)C>[NH2:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[N:4][C:3]=1[NH:17][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 794345-Amino-4,6-dichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22143697HCID 22143697, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part A. A solution of 5-amino-4,6-dichloropyrimidine (24.6 g, 150 mmol), 4-methoxybenzylamine (20.0 mL, 150 mmol) and diisopropylethylamine (30.0 mL, 172 mmol) in ethanol (200 mL) was heated to ref lux for 4 days. After cooling, the solution was evaporated and the residue partitioned between water and ethyl acetate. The organic layer was washed with more water and brine, and the three aqueous phases were back-extracted in sequence with ethyl acetate. The extracts were combined, dried over sodium sulfate, filtered and evaporated. The resulting solid was triturated with ether, collected by filtration and dried under vacuum to afford pure product, 5-amino-4-chloro-6-(4-methoxybenzylamino)pyrimidine. m.p. 187-188° C. TLC RF 0.11 (30:70 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): Δ 8.12 (1H, s), 7.33 (2H! d, J=9.0 Hz), 6.89 (2H, d, J=9.0 Hz), 5. 01 (1H, br), 4. 61 (2H, d, J=5. 1 Hz), 3. 81 (3H, s), 3.35 (2H, br). MS (NH3-CI): m/e 268 (4), 267 (31), 266 (15), 265 (100).

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic layer was washed with more water and brine
  5. extractionthe three aqueous phases were back-extracted in sequence with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting solid was triturated with ether
  10. filtrationcollected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-6d8e3961a18743a294e9f81febe93cf8
Source dataset
uspto-grants-2006_05
Patent number
US07045529B2

Reaction notes

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