Benzylamine → HCID 118157958, compound

HRID 2200871Notes

Reaction equation

HRID 2200871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)Cl.O>[CH2:23]([NH:30][C:13]([C:12]1[C:7]([NH:6][CH2:5][C:4]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:2]([Cl:1])[CH:3]=2)=[N:8][C:9]([S:16][CH3:17])=[N:10][CH:11]=1)=[O:15])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 118157958HCID 118157958, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (60 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio) pyrimidine-5-carboxylic acid (1.0 g, 2.95 mmol), benzylamine (379 mg, 3.54 mmol) and HATU (1.35 g, 3.54 mmol). DIEA (1 mL, 5.9 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 h, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate. Then the solvent was removed by rotary evaporation. The obtained solid was purified by silica gel column chromatography (DCM/methanol=50/1). The product was N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-formamide as a faint yellow solid (800 mg, yield 63%).

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. customThen the solvent was removed by rotary evaporation
  3. customThe obtained solid was purified by silica gel column chromatography (DCM/methanol=50/1)

Sources & evidence

ORD record
ord-c5761483eb234cefb9f1328b6fe78713
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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