Bis-(1H-imidazol-2-YL)-methanone → 5-Chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 2243645Notes

Reaction equation

HRID 2243645 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([NH:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[N:5][C:6]([S:10][CH3:11])=[N:7][C:8]=1[Cl:9].[C:21](C1NC=CN=1)(C1NC=CN=1)=[O:22]>C(Cl)Cl>[Cl:9][C:8]1[N:7]=[C:6]([S:10][CH3:11])[N:5]=[C:4]2[N:12]([C:13]3[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[F:19])[C:21](=[O:22])[NH:1][CH2:2][C:3]=12

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 575305435-(Aminomethyl)-6-chloro-N-(2,6-difluorophenyl)-2-(methylthio)-4-pyrimidinamine

Product 1

HCID 575305005-Chloro-1-(2,6-difluorophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To the solution of 5-(aminomethyl)-6-chloro-N-(2,6-difluorophenyl)-2-(methylthio)-4-pyrimidinamine (0.317 g) in CH2Cl2 (5 mL) was added the mixture of carbonyl diimidazole (0.178 g) in CH2Cl2 (5 mL). The resultant mixture was stirred for about 3 hours at r.t., mixed with CH2Cl2 (10 mL) and washed with HCl (1 N, 2×10 mL) and H2O (20 mL). The organic layers were collected, dried over Na2SO4, filtered and concentrated to provide the title compound (0.279 g, 81%). LC-MS m/z 343 (M+H)+, 1.75 min (ret. time); 1H-NMR (400 MHz, CDCl3) δ 7.44-7.40 (m, 1H), 7.07-7.03 (m, 2H), 5.84 (br, 1H), 4.62 (s, 2H), 2.19 (s, 3H).

Workup

  1. washwashed with HCl (1 N, 2×10 mL) and H2O (20 mL)
  2. customThe organic layers were collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34325deb0d22467693de1ef07be3dea7
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…