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

HRID 459973Notes

Reaction equation

HRID 459973 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18](S(C)=O)=[N:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[C:14]1=[O:28].[CH2:29]([N:31]([CH2:37][CH3:38])[CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH3:30]>>[CH2:29]([N:31]([CH2:37][CH3:38])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:18]1[N:17]=[C:16]2[N:15]([CH2:26][CH3:27])[C:14](=[O:28])[N:13]([C:3]3[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[F:12])[CH2:22][C:21]2=[CH:20][N:19]=1)[CH3:30]

Participants

3

Reactant 2

HCID 117976N,N-Diethyl-1,4-butanediamineHCID 184447943-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Product 1

HCID 117554077-(4-Diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 88.4%

Procedure

7-(4-Diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as described in Example 3 using 0.46 g (1.11 mmol) of 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.32 g (2.22 mmol) of 4-diethylamino-butylamine. The crude product was purified using a gradient of 9:1 ethyl acetate/methanol to 9:0.25:0.25 to 9:0.5:0.25 ethyl acetate/methanol/triethylamine to give 0.4833 g (83%) of the title compound: mp 140° C.–141° C. MS (APCI) (m+1)/z 493.2.

Workup

  1. custom7-(4-Diethylamino-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-82e004982b844b9398cadb1d9ff86302
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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