Aniline → HCID 22125145, compound

HRID 1858324Notes

Reaction equation

HRID 1858324 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]2[C:25]3=[N:26][C:27](S(C)(=O)=O)=[N:28][CH:29]=[C:24]3[CH2:23][N:22]([C:34]3[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:41])C2=O)[CH:15]=1)([CH2:12][CH3:13])[CH2:10][CH3:11])(C)(C)C.[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54]>ClCCl>[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54].[NH2:7][CH2:8][C:9]([C:14]1[CH:15]=[C:16]([N:20]2[C:25]3=[N:26][C:27]([NH:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[N:28][CH:29]=[C:24]3[CH2:23][N:22]([C:34]3[C:35]([Cl:41])=[CH:36][CH:37]=[CH:38][C:39]=3[Cl:40])[C:53]2=[O:55])[CH:17]=[CH:18][CH:19]=1)([CH2:12][CH3:13])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 53796428HCID 53796428, compound

Product 1

HCID 22125145HCID 22125145, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 400 mg (0.62 mmol) of (2-[3-[3-(2,6-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-2-ethyl-butyl)-carbamic acid tert-butyl ester and 600 mg (6.5 mmol) of aniline was heated at 140° C. for 45 minutes and cooled. The residue was dissolved in 20 ml of a 1:1 mixture of dichloromethane and trifluoroacetic acid. After 10 minutes the mixture was evaporated and the product purified by flash chromatography on silica gel using a gradient elution from dichloromethane/methanol 98:2 to dichloromethane/methanol 95:5. Product-containing fractions were evaporated and the residue dissolved in 4 ml of dichloromethane. The product was precipitated by the addition of pentane and subsequently filtered and dried to give 65 mg (19%) of 1-[3-(1-aminomethyl-1-ethyl-propyl)-phenyl]-3-(2,6-dichloro-phenyl)-7-phenylamino-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one trifluoroacetate as a white solid of melting point 232° C.

Workup

  1. temperaturecooled
  2. customAfter 10 minutes the mixture was evaporated
  3. customthe product purified by flash chromatography on silica gel using
  4. washa gradient elution from dichloromethane/methanol 98:2 to dichloromethane/methanol 95:5
  5. customProduct-containing fractions were evaporated
  6. dissolutionthe residue dissolved in 4 ml of dichloromethane
  7. customThe product was precipitated by the addition of pentane
  8. filtrationsubsequently filtered
  9. customdried

Sources & evidence

ORD record
ord-f42e594d59444311bc03618e6493604f
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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