N,N-Diethylaniline → HCID 10192635, compound

HRID 1984312Notes

Reaction equation

HRID 1984312 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6](O)[C:7]3[CH2:12][CH2:11][NH:10][C:8]=3[N:9]=2)[CH2:3][CH2:2]1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:6]1[C:7]2[CH2:12][CH2:11][NH:10][C:8]=2[N:9]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:5]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychloride2×HCID 178517397HCID 178517397, compound

Product 1

HCID 10192635HCID 10192635, compound

Conditions

Temperature
120 °C

Procedure

2-cyclopropyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-ol 48 (0.5 g, 2.8 mmol) is suspended in phosphorus oxychloride (0.7 ml). A mixture of N,N-diethylaniline (0.46 g, 3.1 mmol) and phosphorus oxychloride (0.7 ml) is added dropwise to the suspension at room temperature. The resulting mixture is stirred at 120° C. for 3 h. The solution is poured onto crushed ice and extracted two times with dichloromethane. The aqueous layer is alkalinized (pH 10) and extracted four times with dichloromethane. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo. The crude mixture (370 mg, 68%, 91% purity) is used in the next step without further purification due to the unstability of the compound.

Workup

  1. additionis added dropwise to the suspension at room temperature
  2. additionThe solution is poured
  3. customonto crushed ice
  4. extractionextracted two times with dichloromethane
  5. extractionextracted four times with dichloromethane
  6. dry with materialThe combined organic layers are dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture (370 mg, 68%, 91% purity) is used in the next step without further purification due to the unstability of the compound

Sources & evidence

ORD record
ord-256b07f92e6145e3ab38aa7d4f0d6a4a
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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