Ammonia → 5,6-Diamino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 1664503Notes

Reaction equation

HRID 1664503 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6](=[S:13])[NH:5][C:4](=[O:14])[C:3]=1[N:15]=O.N.O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(=O)C>[NH2:15][C:3]1[C:4](=[O:14])[NH:5][C:6](=[S:13])[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24489Sodium DithioniteHCID 576001906-Amino-5-nitroso-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 576002545,6-Diamino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 86.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 6-amino-1-pentyl-5-nitroso-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (6.4 g, 0.0264 mol), aqueous ammonia (60 mL, 0.60 mol) and water (60 mL) at 75° C. was added sodium dithionite (9.0 g, 0.050 mol) in small portions. After the addition was complete, the color of the solution changed from red to pale yellow. After stirring at 75° C. for another 5 mins, a precipitate was formed. Stirring was continued at room temperature for 1.5 h. The solution was then neutralized with 10% acetic acid (150 mL). The solid was filtered and washed with water to yield the product (4.5 g, 86.1%). LCMS calculated for C9H17N4OS: (M+H) 229.1. found 229.1.

Workup

  1. additionAfter the addition
  2. customa precipitate was formed
  3. stirringStirring
  4. waitwas continued at room temperature for 1.5 h
  5. filtrationThe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-82b3a3842615437fb9898c4652d3eb45
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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