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Potassium Carbonate → 3-[5-Cyclopropyl-3-(2,6-difluoro-pyridin-4-ylmethyl)-2,6-dioxo 1,2,3,6tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile

HRID 426255
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HRID 426255 반응식
[CH:1]1([C:4]2[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=2[C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:36]=[C:35]([F:37])[N:34]=[C:33]([F:38])[CH:32]=1.[I-].[Li+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([C:4]2[C:9](=[O:10])[NH:8][C:7](=[O:11])[N:6]([CH2:30][C:31]3[CH:36]=[C:35]([F:37])[N:34]=[C:33]([F:38])[CH:32]=3)[C:5]=2[C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])[CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 591846774-(Bromomethyl)-2,6-difluoropyridineHCID 591847043-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

생성물 1

HCID 250296833-[5-Cyclopropyl-3-(2,6-difluoro-pyridin-4-ylmethyl)-2,6-dioxo 1,2,3,6tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile
수율 9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (10 mg, 0.034 mmol) was dissolved in 0.5 mL DMF. Potassium carbonate (4.7 mg, 1 eq.) and 4-bromomethyl-2,6-difluoro-pyridine (7 mg, 1 eq.) were added to the reaction, followed by lithium iodide (4.5 mg, 1 eq.) The reaction was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated down and purified by reversed phase HPLC (MeCN/water) to give white powder (1.2 mg, 9%). LC-MS shows 420.9 (M−1). 1H NMR (300 MHz, CD3OD): δ 8.40 (s, 1H), 7.97 (s, 1H), 7.79 (s, 1H), 7.76 (s, 1H), 6.58 (s, 2H), 4.85 (s, 2H), 2.44 (s, 3H), 1.01 (m, 1H), 0.72 (m, 3H), 0.43 (m, 1H).

후처리

  1. washby washing with brine
  2. concentrationThe organic layer was concentrated down
  3. custompurified by reversed phase HPLC (MeCN/water)

출처 및 근거

ORD 기록
ord-e07ea8ff283443009773b7099daacf2c
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106064B2

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