Tetrahydrofuran → HCID 59427331, compound

HRID 1042811Notes

Reaction equation

HRID 1042811 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:24][N:23]=1.C1COCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CS(C)=O.CCCCCC>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[N:18][C:17]([NH:20][C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[N:24][N:23]=4)=[N:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 2721091-Chloro-4-phenylphthalazineHCID 2733832Lithium HexamethyldisilazideHCID 86628668HCID 86628668, compound

Product 1

HCID 59427331HCID 59427331, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

N5-(7-methoxy-1,5-naphthyridin-4-yl)pyrimidine-2,5-diamine (90 mg, 335 μmol), 1-chloro-4-phenylphthalazine (97 mg, 403 μmol), THF (1677 μl, 335 μmol), and LiHMDS (1006 μl, 1006 μmol) were added into a pressure tube. The mixture was stirred at RT for 10 min. A red solution was formed. The tube was placed in a preheated oil bath at 100° C. After 1 h, LCMS showed complete conversion of SM to product. The reaction was cooled to rt. Hexane was added to induce the product to precipitate out of the reaction mixture. The resulting red solid was filtered with an aid of hexane. LCMS confirmed that the solid was the product. The product was purified by performing a column chromatography on silica gel using 60:40 CH2Cl2:(90:10:1 CH2Cl2:MeOH:NH4OH). Yellow solid was obtained. LCMS confirmed product. HPLC showed 96% pure. 1H NMR showed rotamers. Note: this cmpd was slightly soluble in DMSO at rt. MS Calcd for C27H20N8O: [M]+=472. Found: [M+H]+=473.

Workup

  1. customA red solution was formed
  2. customThe tube was placed in a preheated oil bath at 100° C
  3. waitAfter 1 h
  4. temperatureThe reaction was cooled to rt
  5. customto precipitate out of the reaction mixture
  6. filtrationThe resulting red solid was filtered with an aid of hexane
  7. customThe product was purified
  8. customYellow solid was obtained

Sources & evidence

ORD record
ord-85636af36c6848179a025b238e861f32
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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