Potassium Iodide → tert-Butyl 3-{3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8(5H)-yl)ethyl]5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate

HRID 1499714노트

반응식

HRID 1499714 반응식
[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Cl:21][C:22]1[C:23]([CH3:44])=[C:24]([CH:33]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34]2)[C:25]([O:31][CH3:32])=[C:26]([CH:28](Cl)[CH3:29])[CH:27]=1>CN(C)C=O.O>[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][N:8]([CH:28]([C:26]3[C:25]([O:31][CH3:32])=[C:24]([CH:33]4[CH2:34][N:35]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH2:36]4)[C:23]([CH3:44])=[C:22]([Cl:21])[CH:27]=3)[CH3:29])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 57067884-aminopyrido[2,3-d]pyrimidin-5(8H)-oneHCID 86677627tert-Butyl 3-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]azetidine-1-carboxylate

생성물 1

HCID 86677653tert-Butyl 3-{3-[1-(4-amino-5-oxopyrido[2,3-d]pyrimidin-8(5H)-yl)ethyl]5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
140 °C

실험 절차

To a mixture of 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one (from VWR) (8.6 mg, 0.053 mmol), cesium carbonate (26 mg, 0.080 mmol) and potassium iodide (0.89 mg, 0.0053 mmol) in N,N-dimethylformamide (0.2 mL) was added tert-butyl 3-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]azetidine-1-carboxylate (20 mg, 0.05 mmol, from Example 1, step 5, racemic intermediate). The mixture was stirred at 140° C. for 1 hour, then cooled and was diluted with water, extracted with ether. The organic layers were dried over MgSO4 and concentrated to afford the crude product which was used in the next step directly. LCMS calculated for C25H31ClN5O4 (M+H)+: m/z=500.2; Found: 500.1.

후처리

  1. temperaturecooled
  2. extractionextracted with ether
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a622b0ccd441437690dffc798926c91e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199982B2

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