Ammonia → HCID 10541163, compound

HRID 1359432Notes

Reaction equation

HRID 1359432 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:15]2[C:14](=O)[NH:13][C:12]([S:17][CH3:18])=[N:11][C:10]=2[NH:9][CH:8]=1)(=[O:3])[CH3:2].N.P(Cl)(Cl)([Cl:22])=O>>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:15]2[C:14]([Cl:22])=[N:13][C:12]([S:17][CH3:18])=[N:11][C:10]=2[NH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 135411215HCID 135411215, compound

Product 1

HCID 10541163HCID 10541163, compoundYield 54%

Conditions

Temperature
47.5 °C

Procedure

The above pyrrolopyrimidinone (1.2) (3.7 g, 13.8 mmol) was suspended in phosphoryl chloride (20 ml) and the solution heated at 45-50° C. overnight. The solution was cooled and poured onto ice and stirred for 10 mins and then neutralised with concentrated ammonia solution. The solid was filtered and recrystallised from methanol to give a yellow-brown solid which was chromatographed (CHCl3/2% MeOH) to give the product as a pale brown solid, yield 1.3 g. Unreacted starting material was eluted from the column in CHCl3/5% MeOH, yield 1.44 g. Overall yield 54%. δH ([2H6]-DMSO) 12.24 (1 H, br s, NH), 7.38 (1 H, s, 6-H), 4.26 (2 H, t J 6.8 Hz, OCH2), 3.08 (2 H, t J 6.8 Hz, OCH2CH2), 2.52 (3 H, s, CH3S), 1.98 (3 H, s, CH3CO) ppm. UV λmax (nm) 314 (4800), 254 (28300), 222 (13000). pH 12 λmax 291 (5100), 257 (26700). Accurate mass measurement 285.0339, C11H12CIN3O2S requires 285.0356.

Workup

  1. temperatureThe solution was cooled
  2. additionpoured onto ice
  3. filtrationThe solid was filtered
  4. customrecrystallised from methanol
  5. customto give a yellow-brown solid which
  6. customwas chromatographed (CHCl3/2% MeOH)

Sources & evidence

ORD record
ord-f19052dbda8c4571a90483c4d065ac8a
Source dataset
uspto-grants-2003_07
Patent number
US06600028B1

Reaction notes

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