2-Methoxyethylamine → HCID 59446934, compound

HRID 1946784Notes

Reaction equation

HRID 1946784 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[CH3:27][O:28][CH2:29][CH2:30][NH2:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][NH:31][CH2:30][CH2:29][O:28][CH3:27])=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 2724942TriacetoxyborohydrideHCID 59446872HCID 59446872, compound2×

Product 1

HCID 59446934HCID 59446934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-((cyclopropylmethyl)(propyl)amino)-N-(4-formyl-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 29, 100 mg; 0.28 mmol) in DCM (5 ml) was treated with 2-methoxyethanamine (Aldrich, 112.7 mg; 0.42 mmol) followed by polymer supported triacetoxy borohydride (150 mg). After stirring for 15 hours the mixture was filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as an off-white solid.

Workup

  1. filtrationwas filtered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography (silica)
  4. washeluting with petroleum ether containing
  5. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-9f5603e5722f4d04b9c08cb72438a6d2
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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