4-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINE → Ethyl[2-[2-(2,4-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetate

HRID 573483Notes

Reaction equation

HRID 573483 reaction equation
O=[C:2]1[N:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2[N:14]=[CH:15][CH:16]=[CH:17][C:5]=2[C:4](=[O:18])[NH:3]1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH2:27][CH2:28]C(=N)N.FC(F)(F)C1C=CC(C2C=CC(CN)=CC=2)=CC=1.CC(N1CCC(=O)CC1)(C)C(OC)=O>>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH2:27][CH2:28][C:2]1[N:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2[N:14]=[CH:15][CH:16]=[CH:17][C:5]=2[C:4](=[O:18])[N:3]=1

Participants

5

Reactant 4

HCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 59264606HCID 59264606, compoundHCID 675423773-(2,4-Difluorophenyl)propanimidamideHCID 86624763ethyl (2,4-dioxo-3,4-dihydropyrido[2,3-d]pyrimidin-1(2H)-yl)acetate

Product 1

HCID 59707037Ethyl[2-[2-(2,4-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetate

Procedure

A mixture of ethyl (2,4-dioxo-3,4-dihydropyrido[2,3-d]pyrimidin-1(2H)-yl)acetate (WO 02/30911, Intermediate B52) (40.8 g, 1.2 equiv) and 3-(2,4-difluorophenyl)propanimidamide (made by methods analogous to those described for the 2,3-difluoro isomer, Intermediates A1 to A3 of WO 02/30911) (30.0 g, 1 equiv) was fused in a 150° C. oil bath for 25 min, then cooled quickly to room temperature in a water bath. Chromatography (silica, crude product loaded in DCM and eluted with 50-100% ethyl acetate in hexane) gave the desired product (43.56 g).

Workup

  1. customwas fused in a 150° C.
  2. customfor 25 min
  3. washChromatography (silica, crude product loaded in DCM and eluted with 50-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-58cae54f531443078306bfaac6a03501
Source dataset
uspto-grants-2015_05
Patent number
US09029383B2

Reaction notes

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