Dimethylformamide → HCID 22736319, compound

HRID 51495Notes

Reaction equation

HRID 51495 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C[N:25]([CH3:28])C=O>>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:28]#[N:25])=[CH:15][CH:16]=3)=[CH:9][N:8]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 22736345HCID 22736345, compound

Product 1

HCID 22736319HCID 22736319, compound

Conditions

Temperature
120 °C

Procedure

A warm solution of 4-[4-amino-7-(4-tetrahydropyranyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]phenol (0.082 g) in dimethylformamide (3.4 ml) was added to a The vial was flushed with nitrogen then sealed. The mixture was shaken at 120° C. for 6 hours and then left to cool to ambient temperature over 16 hours. The mixture was diluted with water (11 ml) and then extracted with ethyl acetate to give 2-[4-(4-amino-7-(4-tetrahydropyranyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]benzonitrile, m.p. 125° C. (softens).

Workup

  1. customwas flushed with nitrogen
  2. customthen sealed
  3. waitleft
  4. temperatureto cool to ambient temperature over 16 hours
  5. additionThe mixture was diluted with water (11 ml)
  6. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-1299e544c9de4c0aa495e3534808d93a
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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