Trifluoroacetic acid → HCID 178447261, compound

HRID 1639013Notes

Reaction equation

HRID 1639013 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].FC(F)(F)C(O)=O>[Pt]=O>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH:23]([C:26]([OH:28])=[O:27])[CH2:24][CH2:25]3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178447251HCID 178447251, compound

Product 1

HCID 178447261HCID 178447261, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

Five grams of 2-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine described in European Pat. Application No. 87308921.3) and 1.60 g. of platinum oxide in 200mL. of trifluoroacetic acid were hydrogenated in a Parr apparatus at ambient temperature and 60 psi for 24 hours. Removal of the catalyst by filtration and concentration of the filtrate yielded 2-pivaloylamino-4-hydroxy-6-[2-(4-carboxycyclohex-1-yl)ethyl]-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine as a white solid which was further purified by column chromatography (Waters 200) eluting with 1:9 methanol:dichloromethane. m.p. 218°-234° C. Anal. Calc. for C21H32N4O4 : C, 63.35; H, 7.97; N, 13.85. Found: C, 63.30; H, 7.48; N, 13.57.

Workup

  1. customwere hydrogenated in a Parr apparatus at ambient temperature
  2. customRemoval of the catalyst
  3. filtrationby filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-17e1ca81326c495ba88eda72c49f525a
Source dataset
uspto-grants-1989_11
Patent number
US04882333

Reaction notes

Loading…