Dimethylformamide → Methyl 1-(2-ethoxyethyl)-5,7-dioxo-4,5,6,7-tetrahydro-1h-pyrazolo[4,3-d]pyrimidine-3-carboxylate

HRID 2401304Notes

Reaction equation

HRID 2401304 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([O:17][CH3:18])=[O:16])=[N:4][N:5]([CH2:10][CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7](=[O:9])[NH2:8].CN(C)[CH:21]=[O:22]>>[CH2:13]([O:12][CH2:11][CH2:10][N:5]1[C:6]2[C:7](=[O:9])[NH:8][C:21](=[O:22])[NH:1][C:2]=2[C:3]([C:15]([O:17][CH3:18])=[O:16])=[N:4]1)[CH3:14]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 58935554Methyl 4-amino-5-carbamoyl-1-(2-ethoxyethyl)-1h-pyrazole-3-carboxylate

Product 1

HCID 53438882Methyl 1-(2-ethoxyethyl)-5,7-dioxo-4,5,6,7-tetrahydro-1h-pyrazolo[4,3-d]pyrimidine-3-carboxylate

Procedure

A solution of the amide of step 4 (570 mg, 3.38 mmol) in N,N-dimethylformamide (30 mL) was treated with N,N′-carbonyldiimidazole (658 mg, 4.06 mmol) and the reaction mixture stirred at room temperature for 1 hour and then at 90° C. for 18 hours. The reaction mixture was concentrated in vacuo and the crude product suspended in acetone and sonicated for 30 minutes. The solid product was filtered off and dried in vacuo to yield the dione product. 1H NMR (DMSO-D6, 400 MHz) δ: 1.02 (t, 3H), 3.37 (m, 2H), 3.77 (m, 2H), 3.83 (s, 3H), 4.63 (m, 2H), 10.75 (s, 1H), 11.40 (s, 1H). MS ES− m/z 281 [M-H]−.

Workup

  1. waitat 90° C. for 18 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customsonicated for 30 minutes
  4. filtrationThe solid product was filtered off
  5. customdried in vacuo
  6. customto yield the dione product

Sources & evidence

ORD record
ord-1884dcf78ab8472887c0bc26f434d363
Source dataset
uspto-grants-2014_08
Patent number
US08796287B2

Reaction notes

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