5,6-Diamino-1,3-dimethyluracil → HCID 58762837, compound

HRID 858049Notes

Reaction equation

HRID 858049 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=1[NH2:26].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:18])[NH:19][C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[NH2:26])=[CH:13][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 795015,6-Diamino-1,3-dimethyluracilHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acid

Product 1

HCID 58762837HCID 58762837, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (4-tert-butoxycarbonylamino-phenyl)-acetic acid (0.825 mmol) and crude 5,6-diamino-1,3-dimethyl-1H-pyrimidine-2,4-dione (0.75 mmol) in N,N-dimethylformamide (3 mL) under argon at 25° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(0.825 mmol) and 4-dimethylaminopyridine (0.15 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was triturated with water and the resulting solid collected by filtration, washed well with water and dried in vacuo to afford crude {4-[(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-methyl]-phenyl}-carbamic acid tert-butyl ester as a light beige solid which was of sufficient purity for subsequent use without additional purification (87%).

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. customThe residue was triturated with water
  3. filtrationthe resulting solid collected by filtration
  4. washwashed well with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-11d19bd8e16c4b27b666cec2b11b9c65
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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