Aniline → HCID 22125076, compound

HRID 1858290Notes

Reaction equation

HRID 1858290 reaction equation
C(S([C:11]1[N:16]=[C:15]2[N:17]([CH2:29][C:30]3[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=3)[C:33]([O:35][CH3:36])=[O:34])[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)(=O)=O)C1C=CC=CC=1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[NH:40]([C:11]1[N:16]=[C:15]2[N:17]([CH2:29][C:30]3[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=3)[C:33]([O:35][CH3:36])=[O:34])[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22125023HCID 22125023, compound

Product 1

HCID 22125076HCID 22125076, compoundYield 20%

Conditions

Temperature
100 °C

Procedure

A mixture of 0.655 g (1.1 mmol) of methyl 3-[[7-benzylsulfonyl-3-(2-bromophenyl)-1,2,3,4-tetrahydro-2-oxopyrimido[4,5-d]pyrimidin-1-yl]methyl]benzoate and 0.55 ml (6 mmol) of aniline was heated at 100° C. for 2 hours. The reaction mixture was partitioned between dichloromethane(10 ml) and 2M hydrochloric acid (10 ml) and the dichloromethane layer separated, washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as the eluent. Product containing fractions were combined and evaporated to give 120 mg (20%) of methyl 3-[[7-anilino-3-(2-bromophenyl)-1,2,3,4-tetrahydro-2-oxopyrimido[4,5-d]pyrimidin-1-yl]methyl]benzoate as a white solid of melting point 79-82° C. [Mass spectrum (ESI) MH+ =546].

Workup

  1. customThe reaction mixture was partitioned between dichloromethane(10 ml) and 2M hydrochloric acid (10 ml)
  2. customthe dichloromethane layer separated
  3. washwashed with saturated aqueous sodium bicarbonate (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as the eluent
  8. additionProduct containing fractions
  9. customevaporated

Sources & evidence

ORD record
ord-1aef7605c3ab47a2be470f53cb3c67bb
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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