Triethylamine → 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 571705Notes

Reaction equation

HRID 571705 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[C:10]([CH:11]=O)=[C:9](Cl)[N:8]=[CH:7][N:6]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:4][C:5]1[N:6]=[CH:7][N:8]=[C:9]2[NH:2][N:3]=[CH:11][C:10]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineYield 830.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrazine hydrate (11.5 mL, 23.7 mmol) was slowly added to a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (40.0 g, 22.6 mmol) and triethylamine (30 mL, 22 mmol) in 1,4-dioxane (600 mL) with cooling to maintain an internal temperature below 20° C. After the addition was completed, the reaction was warmed to rt. After 1 hr, the reaction was filtered. The solvent was removed in vacuo to afford the title intermediate (29 g, 83%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ14.52 (br. s, 1H), 8.83 (s, 1H), 8.45 (s, 1H). MS m/z 155 [M+1]+.

Workup

  1. temperaturewith cooling
  2. temperatureto maintain an internal temperature below 20° C
  3. additionAfter the addition
  4. filtrationthe reaction was filtered
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1e773c606d034803aecaf02980c39d58
Source dataset
uspto-grants-2015_05
Patent number
US09029359B2

Reaction notes

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