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

HRID 1516295Notes

Reaction equation

HRID 1516295 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 title product.

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

Sources & evidence

ORD record
ord-75b2f5d8bae9443b8adcc2f7cd670ca6
Source dataset
uspto-grants-2012_07
Patent number
US08227475B2

Reaction notes

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