Diethyl Ether → HCID 178474470, compound

HRID 1199812Notes

Reaction equation

HRID 1199812 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:13])[C:5]2[CH:11]=[C:10]([I:12])[CH:9]=[N:8][C:6]=2[N:7]=1.[CH3:14][CH2:15][O:16]CC>CN(C)C1C=CN=CC=1.C(OC(=O)C)(=O)C>[C:15]([NH:1][C:2]1[N:3]=[C:4]([OH:13])[C:5]2[CH:11]=[C:10]([I:12])[CH:9]=[N:8][C:6]=2[N:7]=1)(=[O:16])[CH3:14]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 178508862HCID 178508862, compound

Product 1

HCID 178474470HCID 178474470, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Analogously, a mixture of 0.52 g of 2-amino-4-hydroxy-6-iodopyrido[2,3-d]pyrimidine and 0.03 g of 4-dimethylaminopyridine in 10 ml of acetic anhydride is heated under reflux under nitrogen for 3 hours. After cooling the reaction mixture to room temperature, anhydrous ether is added, and the reaction mixture filtered to give 0.52 g (87%) of 2-acetamido-4-hydroxy-6-iodopyrido[2,3-d]pyrimidine as a tan colored solid: m.p. >280° C.; NMR (DMSO-d6, 80 MHz) delta 2.18 (s, 3H), 8.67 (d, 1H, J=2.5 Hz), 9.02 (d, 1H, J=2.5 Hz); M/S 330 (M+), 315 and 288.

Workup

  1. temperatureis heated
  2. temperatureunder reflux under nitrogen for 3 hours
  3. filtrationthe reaction mixture filtered

Sources & evidence

ORD record
ord-6510a9445dc44fe29c8dc40561dbf663
Source dataset
uspto-grants-1990_02
Patent number
US04902796

Reaction notes

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