Potassium Carbonate → (2S,4S)-1-tert-butyl 2-methyl 4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1,2-dicarboxylate

HRID 516171Notes

Reaction equation

HRID 516171 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[C:21]3[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=3[NH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:23][O:24][C:25]([C@@H:27]1[CH2:31][C@@H:30](OS(C)(=O)=O)[CH2:29][N:28]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:26].[H-].[Na+].COC1C=C(C#CC2C3C(=NC=NC=3N)NN=2)C=C(OC)C=1.CS(OC1CCN(C(OC(C)(C)C)=O)C1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CN1C(=O)CCC1>[NH2:22][C:20]1[C:21]2[C:13]([C:12]#[C:11][C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:14][N:15]([C@@H:30]3[CH2:29][N:28]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:27]([C:25]([O:24][CH3:23])=[O:26])[CH2:31]3)[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

9

Reactant 6

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 4139999Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylateHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 898708605-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 178489940HCID 178489940, compound

Product 1

HCID 89871046(2S,4S)-1-tert-butyl 2-methyl 4-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In accordance with Example 1 (Step 3), except that the 5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine obtained in Step 4, the (2S,4R)-4-(methylsulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester obtained in Step 5, sodium hydride, and NMP were individually used in place of 3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate, potassium carbonate, and DMF, the title compound was obtained as a colorless, amorphous substance. Physical properties: m/z [M+H]+ 522.4

Sources & evidence

ORD record
ord-313195803c404157b23a0d53aed8d216
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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