Ammonia → 2-amino-6-(3-amino-4-fluorophenyl)-8-cyclopropylpyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1930288Notes

Reaction equation

HRID 1930288 reaction equation
Cl[C:2]1[C:7]([C:8](OCC)=O)=[CH:6][N:5]=[C:4](SC)[N:3]=1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.[NH2:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28]([O:30]CC)=O)[CH:23]=[CH:24][C:25]=1[F:26].[NH3:33]>O1CCOCC1>[NH2:33][C:4]1[N:5]=[CH:6][C:7]2[CH:8]=[C:27]([C:22]3[CH:23]=[CH:24][C:25]([F:26])=[C:20]([NH2:19])[CH:21]=3)[C:28](=[O:30])[N:18]([CH:15]3[CH2:17][CH2:16]3)[C:2]=2[N:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 69828CyclopropylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 68983893Ethyl 2-(3-amino-4-fluorophenyl)acetate

Product 1

HCID 690884892-amino-6-(3-amino-4-fluorophenyl)-8-cyclopropylpyrido[2,3-d]pyrimidin-7(8H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using procedures analogous to Example C2 and Example A2, ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, cyclopropyl amine, ethyl 2-(3-amino-4-fluorophenyl)acetate (prepared by the method of Kuse et al. Tetrahedron (2005), 67, 5754-5762) and 0.5 M ammonia in dioxane (2 ml) were combined to afford 2-amino-6-(3-amino-4-fluorophenyl)-8-cyclopropylpyrido[2,3-d]pyrimidin-7(8H)-one as an off-white solid (67 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.57 (s, 1H), 7.73 (s, 1H), 7.15 (brs, 1H), 7.06 (dd, J=9.2 Hz, 2.4 Hz, 1H), 6.99 (dd, J=11.2 Hz, 11.6 Hz, 1H), 6.75-6.71 (m, 1H), 2.88-2.82 (m, 1H), 1.18-1.13 (m, 2H), 0.83-0.78 (m, 2H); MS (ESI) m/z: 312.0 (M+H+).

Sources & evidence

ORD record
ord-ca4624e141894c4bb6868095f3aa5fa2
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…