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 1697957Notes

Reaction equation

HRID 1697957 reaction equation
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

Participants

8

Reactant 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 59239275Pyrido[3,4-d]pyriMidine-7(6H)-carboxylic acid, 2-chloro-5,8-dihydro-4-[(3S)-3-Methyl-4-Morpholinyl]-, 1,1-diMethylethyl ester

Product 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)-carboxylateYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-291fcdd43744476eb5ef44b30e3b9a91
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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