Water → Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate

HRID 1410015Notes

Reaction equation

HRID 1410015 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([OH:36])[CH:27]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CI.[C:42]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:39]=[CH:38][S:37][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]([C:26]4[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([O:36][CH3:42])[CH:27]=4)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68379322Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate

Product 1

HCID 68379417Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate (100 mg, 0.18 mmol) in 2 mL of DMF were added MeI (38 mg, 0.27 mmol) and K2CO3 (37 mg, 0.27 mmol) at room temperature, and then the mixture was stirred for 16 hours. The mixture was poured into water and extracted with EtOAc (3×5 mL). The organic layer was washed with 0.1 N HCl (5 mL) and brine. The organic layer was dried over Na2SO4. After filtration and concentration, the crude methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-methoxybenzoate was obtained and used the next step without purification (80 mg, 78%). LC-MS: 565 [M+H]+, tR=1.48 min.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. washThe organic layer was washed with 0.1 N HCl (5 mL) and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-d7cf4655b95745f6bb76157bdd4fd80b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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