1-Butanol → HCID 136341860, compound

HRID 1797419Notes

Reaction equation

HRID 1797419 reaction equation
Cl.N[C:3]1([Si:11]([CH3:19])([CH3:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH:5]([CH2:8]O)[C:4]1=[CH2:10].[NH2:20][C:21]1[NH:22][C:23](=[O:31])[C:24]([N+:28]([O-:30])=[O:29])=[C:25]([NH2:27])[N:26]=1.C([OH:36])CCC.C(N(CC)CC)C>O>[NH2:20][C:21]1[NH:22][C:23](=[O:31])[C:24]([N+:28]([O-:30])=[O:29])=[C:25]([NH:27][CH:6]2[CH2:7][CH:3]([Si:11]([CH3:19])([CH3:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:4]([CH2:10][OH:36])[C:5]2=[CH2:8])[N:26]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 86594451HCID 86594451, compoundHCID 1354616622,6-diamino-5-nitropyrimidin-4(3H)-one

Product 1

HCID 136341860HCID 136341860, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 3-necked 500 mL round bottomed flask equipped with stirrer, temperature probe and reflux condenser was charged with the amine 69 (1.49 g, 5 mmol), 2,4-diamino-5-nitropyrimidin-6-one (1.56 g, 5.35 mmol) and n-butanol (20 mL). The resultant thin slurry was subjected to heating at 40–45° C. over 15 minutes. Triethylamine (0.71 mL, 5.1 mmol) was added slowly over a period of 2 minutes. The reaction mixture was stirred at about 70° C. for 1 h. HPLC data showed that the reaction was almost complete. At this point, five washes of 25 mL of water was given to the reaction mixture at 70° C. The last wash was almost colorless. The crude product, 70, in n-butanol was used without further purification in the next reaction.

Workup

  1. customA 3-necked 500 mL round bottomed flask equipped with stirrer
  2. temperaturetemperature probe and reflux condenser
  3. temperatureto heating at 40–45° C. over 15 minutes
  4. customwas given to the reaction mixture at 70° C
  5. washThe last wash
  6. customThe crude product, 70, in n-butanol was used without further purification in the next reaction

Sources & evidence

ORD record
ord-8c6a934906d143b991c7b62a1b0e5990
Source dataset
uspto-grants-2006_04
Patent number
US07034152B2

Reaction notes

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