Urea → Urea, N-phenyl-N'-propyl-

HRID 2258482Notes

Reaction equation

HRID 2258482 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N)CC.NC(N)=O.C(CC(O)=O)#N.N[C:25]1[N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:29](=[O:37])[N:28]([CH2:38][CH2:39][CH3:40])[C:27](=[O:41])[CH:26]=1>>[CH2:27]([NH:28][C:29]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:37])[CH2:26][CH3:25].[CH3:29][NH:30][C:25]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:9])[N:28]([CH2:38][CH2:39][CH3:40])[C:27](=[O:41])[CH:26]=1

Participants

7

Reactant 5

HCID 1176UreaHCID 7672Phenyl isocyanateHCID 7852PropylamineHCID 9740Cyanoacetic acidHCID 229220916-Amino-1-phenyl-3-propylpyrimidine-2,4(1H,3H)-dione

Product 2

HCID 3604138Urea, N-phenyl-N'-propyl-HCID 22921997HCID 22921997, compound

Procedure

N-Propyl-N'-phenylurea was prepared preliminarily from phenyl isocyanate and propylamine by the same procedure as in Reference Example 1. The urea compound as the starting material was reacted with cyanoacetic acid to form a uracil ring. Subsequently, 6-amino-1-phenyl-3-propyluracil was treated as in Reference Example 2 so that the substituent amino group at the 6-position was converted to a methylamino group to yield 6-methylamino-1-phenyl-3-propyluracil. Using sodium nitrite a nitroso group was introduced into the 5-position of the uracil ring and then reduced with hydrogen gas to prepare 5-amino-6-methylamino-1-phenyl-3-propyluracil.

Workup

  1. customto form a uracil ring

Sources & evidence

ORD record
ord-bde42a93d4ec43799f01e0a58b2c1a1a
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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