HCID 178425225, compound → HCID 178425226, compound

HRID 2206495Notes

Reaction equation

HRID 2206495 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([NH:13][CH2:14][C:15]3[C:16]([OH:23])=[N:17][C:18]([CH3:22])=[CH:19][C:20]=3[CH3:21])=[O:12])=[C:9]([CH3:24])[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:6]=2[N:7]=1>N1CCCC1>[OH:23][C:16]1[C:15]([CH2:14][NH:13][C:11]([C:10]2[C:5]3[CH:4]=[N:3][C:2]([N:8]4[CH2:9][CH2:10][CH2:5][CH2:6]4)=[N:7][C:6]=3[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:9]=2[CH3:24])=[O:12])=[C:20]([CH3:21])[CH:19]=[C:18]([CH3:22])[N:17]=1

Participants

3

Reactant 1

HCID 178425225HCID 178425225, compound

Product 1

HCID 178425226HCID 178425226, compoundYield 123.8%

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

A solution of (R)-2-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (70 mg, 0.15 mmol) in pyrrolidine (1.0 mL) was stirred at 150° C. for 30 minutes under microwave (pressure: 12.2 bar, equipment power: 150 W). The mixture was concentrated in vacuo and purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to afford (R)—N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-methyl-7-(1-phenylethyl)-2-(pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (45 mg, 60.0%). LRMS (M+H) m/z: calcd 484.26. found 484. HPLC purity (214 nm): 97.8%. 1H NMR (400 MHz, CD3OD) δ 8.56 (s, 1H), 7.27-7.20 (m, 5H), 6.06-6.02 (m, 2H), 4.45 (s, 2H), 3.52-3.45 (m, 4H), 2.40 (s, 3H), 2.35 (s, 3H), 2.21 (s, 3H), 2.01-1.94 (m, 7H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-7cfe92628d4645ea9a2ee78221eada13
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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