Ammonium formate → Methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate

HRID 1746650노트

반응식

HRID 1746650 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([N:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH:14]2[CH2:16][CH2:15]2)[N:3]=1.C([O-])=O.[NH4+]>CC(O)C.O.[Pd]>[CH:17]1([N:12]([CH2:13][CH:14]2[CH2:15][CH2:16]2)[C:4]2[N:3]=[CH:2][N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 59446993Methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate2회

생성물 1

HCID 59446889Methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate수율 97.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

A solution of methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 11, 4.77 g; 14.7 mmol) in 150 ml of iPrOH was treated with 780 mg of palladium (10% on C). The suspension was degassed and a solution of ammonium formate (6.96 g; 110 mmol) in 20 ml of water was added. After stirring at RT for 45 minutes, the suspension was filtered on a pad of Celite, the remaining residue was twice rinsed with 50 ml of iPrOH and the combined filtrates were evaporated under reduced pressure. The remaining colorless residue was partitioned between 150 ml of MTBE and 150 ml of water. Both layers were separated. The organic phase was once washed with 100 ml of brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as colorless oil (4.14 g, 97%).

후처리

  1. customThe suspension was degassed
  2. filtrationthe suspension was filtered on a pad of Celite
  3. washthe remaining residue was twice rinsed with 50 ml of iPrOH
  4. customthe combined filtrates were evaporated under reduced pressure
  5. customThe remaining colorless residue was partitioned between 150 ml of MTBE and 150 ml of water
  6. customBoth layers were separated
  7. washThe organic phase was once washed with 100 ml of brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-03132e227e5a4c389063573a25948c90
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150519B2

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