Dimethylformamide → HCID 11952049, compound

HRID 2243659Notes

Reaction equation

HRID 2243659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37].[CH3:38][N:39](C=O)[CH3:40]>C(Cl)Cl.CNC.O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([N:39]([CH3:40])[CH3:38])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 11950096HCID 11950096, compound

Product 1

HCID 11952049HCID 11952049, compound

Reagents, catalysts & solvents 3

HCID 674DimethylamineSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-thiophenecarboxamide, (0.054 g, 0.1 mmol) was dissolved in a mixture of DMF (0.5 mL) and CH2Cl2 (10 mL), and 40% dimethylamine in water (1 mL) was added. The mixture was stirred under argon at room temperature for 3 h. The solvents were pumped off in vacuo. The residue was flash chromatographed on silica gel (10 g) eluted with 10-60% EtOAc/CH2Cl2 to give the title compound as a white amorphous solid. The solid was crystallized from CH2Cl2/hexane to give the title compound as a white crystalline solid. mp 214-215° C.; LC-MS m/z 521 (M+H)+, 2.0 min (ret. time).

Workup

  1. additionwas added
  2. customchromatographed on silica gel (10 g)
  3. washeluted with 10-60% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-d2b4f8bcb3ec4095a4e16419949a6bd5
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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