N,N-Diethyl-1,4-butanediamine → 1-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(3-ethoxy-2,6-difluoro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459991Notes

Reaction equation

HRID 459991 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:30])=[C:6]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16](S(C)=O)=[N:17][CH:18]=3)[N:13]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:12]2=[O:29])[C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2].[CH2:31]([N:33]([CH2:39][CH3:40])[CH2:34][CH2:35][CH2:36][CH2:37][NH2:38])[CH3:32].C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>O1CCOCC1>[CH:24]1([N:13]2[C:14]3=[N:15][C:16]([NH:38][CH2:37][CH2:36][CH2:35][CH2:34][N:33]([CH2:39][CH3:40])[CH2:31][CH3:32])=[N:17][CH:18]=[C:19]3[CH2:20][N:11]([C:6]3[C:7]([F:10])=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[C:5]=3[F:30])[C:12]2=[O:29])[CH2:27][CH2:28][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 117976N,N-Diethyl-1,4-butanediamineHCID 184447953-(3-ethoxy-2,6-difluoro-phenyl)-1-(1-ethyl-propyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneHCID 22328969EtOH ethyl acetate triethylamine

Product 1

HCID 100752511-Cyclopentyl-7-(4-diethylamino-butylamino)-3-(3-ethoxy-2,6-difluoro-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using Procedure K, described above, 0.74 g (1.69 mmol) of 3-(3-ethoxy-2,6-difluoro-phenyl)-1-(1-ethyl-propyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 4-(diethylamino)butylamine in 20 mL of dioxane were reacted. Chromatography with 9:1:0.5 ethyl acetate/ethanol/ triethylamine gave 0.75 g (86%) of the title compound as a solid: mp 129° C.–130° C. 130° C. MS (APCI) (m+1)/z 5127.47. Analysis calculated for C27H38N6F2O2: C, 62.77; H, 7.41; N, 16.27.Found: C, 62.79; H, 7.35; N, 16.10.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d5e9e47280464c72b78f3c7713768875
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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