N,N-Dimethylaniline → HCID 178435386, compound

HRID 1934414Notes

Reaction equation

HRID 1934414 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:8]1[NH:19][C:11]2[NH:12][C:13]([S:17][CH3:18])=[N:14][C:15](=O)[C:10]=2[CH:9]=1)[CH3:7].CN(C)C1C=CC=CC=1>>[CH3:18][S:17][C:13]1[NH:12][C:11]2=[N:19][C:8]([CH2:6][CH3:7])=[CH:9][C:10]2=[C:15]([Cl:3])[N:14]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178435423HCID 178435423, compound

Product 1

HCID 178435386HCID 178435386, compoundYield 89.6%

Conditions

Temperature
95 °C

Procedure

Phosphorous oxychloride (21 mL) was carefully added to a mixture of 5.66 g (27.0 mmol) of 1,7-dihydro-6-ethyl-2-(methylthio)-4H-pyrrolo[2,3-d]pyrimidin-4-one and 1.70 mL of N,N-dimethylaniline. The reaction was heated to 95° C. for 12 hours. At this time the reaction was cooled and concentrated under vacuum. The residue was combined with 60 g of ice and stirred for 1 hour. The solids were collected by filtration, washed with 30 mL of water and suspended in 100 mL of water. The solids were again collected, washed with 30 mL of water, and dried in vacuo (40° C., 10 torr) to provide 5.50 g (89.6%) of 2-(methylthio)-4-chloro-6-ethyl-1H-pyrrolo[2,3-d]pyrimidine as a yellow solid. nmr (500 MHz, dmso-d6) δ1.24 (t, J=7.5 Hz, 3H), 2.52 (s, 3H), 2.70 (q, J=7.5 Hz, 2H), 6.21 (s, 1H), 12.27 (s, 1H)

Workup

  1. temperatureAt this time the reaction was cooled
  2. concentrationconcentrated under vacuum
  3. filtrationThe solids were collected by filtration
  4. washwashed with 30 mL of water
  5. customThe solids were again collected
  6. washwashed with 30 mL of water
  7. customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record
ord-3d8d3fef90b04ed1ac35999dcf3e5d3d
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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