Acetic Acid → HCID 135797460, compound

HRID 1842585Notes

Reaction equation

HRID 1842585 reaction equation
[CH3:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([NH:12]C(=O)OC)=[N:5][C:4]=2[CH:3]=1.CC(O)=O>[OH-].[Na+]>[NH2:12][C:6]1[NH:7][C:8](=[O:11])[C:9]2[NH:10][C:2]([CH3:1])=[CH:3][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135797452Methyl (6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)carbamate

Product 1

HCID 135797460HCID 135797460, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

To a 200 mL round bottomed flask was added 7 (1 g, 4.5 mmol) suspended in 1 N NaOH (35 mL). The reaction mixture was heated at 55° C. for 3 h. The resulting solution was cooled in an ice bath and neutralized with AcOH. The precipitated solid was collected by filtration, washed with brine, and dried in vacuo to afford 0.67 g (92%) of 8 as a white solid: mp 252-254° C.; TLC Rf0.15 (MeOH/CHCl3, 1:5); 1H NMR (DMSO-d6) δ 2.20 (s, 3 H), 5.65 (s, 1 H), 5.65 (s, 2 H), 10.21 (s, 1 H), 11.15 (s, 1 H). Anal. (C7H8N4O0.73H2O) C, H, N.

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with brine
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ec88aef51f534028a27a4dd5bd155fa6
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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