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Potassium Carbonate → (S)-tert-butyl 2-(4-(6-(benzyloxy)pyridin-2-ylamino)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

HRID 1697957
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인쇄 미리보기

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HRID 1697957 반응식
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]2[CH3:25])[C:5]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][C:6]=2[N:7]=1.[CH2:26]([O:33][C:34]1[N:39]=[C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44](B3OC(C)(C)C(C)(C)O3)=[CH:43][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(=O)C.[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(#N)C>[CH2:26]([O:33][C:34]1[N:39]=[C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([C:2]3[N:3]=[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]4[CH3:25])[C:5]4[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][C:6]=4[N:7]=3)=[CH:43][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 582225306-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2-amineHCID 59239275(S)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

생성물 1

HCID 59239075
(S)-tert-butyl 2-(4-(6-(benzyloxy)pyridin-2-ylamino)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate
수율 90%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a mixture of (S)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (by) (54 mg, 0.15 mmol), 6-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2-amine (ow) (prepared in Example 289, 61 mg, 0.15 mmol), Tetrakis(triphenylphosphine)palladium(0) (11.7 mg, 0.0101 mmol), Potassium carbonate (26.8 mg, 0.194 mmol) and Potassium acetate (19.9 mg, 0.203 mmol) was added Acetonitrile (0.56 mL) and Water (0.23 mL) under N2. The reaction was microwaved at 120° C. for 20 minutes. After evaporation of solvents, the residue was purified on a silica gel column to give the desired product (80 mg, 90% yield) as slightly brown powder. The 1H-NMR, TLC and LC-MS were identical to the one in Example 299.

후처리

  1. customThe reaction was microwaved at 120° C. for 20 minutes
  2. customAfter evaporation of solvents
  3. customthe residue was purified on a silica gel column

출처 및 근거

ORD 기록
ord-291fcdd43744476eb5ef44b30e3b9a91
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163763B2

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