Water → HCID 86692148, compound

HRID 527925Notes

Reaction equation

HRID 527925 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]([CH3:31])[C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]3[C:15]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:10]2)=[N:6][CH:7]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.O>CN1C(=O)CCC1>[CH3:31][N:8]([C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10]1)[C:5]1[CH:4]=[N:3][C:2]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 86692149HCID 86692149, compound

Product 1

HCID 86692148HCID 86692148, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (R)-5-bromo-N-methyl-N-(1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)pyrazin-2-amine (0.099 mmol) and morpholine (1.5 mL) in NMP (0.5 mL) was stirred at 195° C. for 2 hours in a microwave reactor. After cooling to the ambient temperature, it was poured into water, and extracted with EtOAc. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-098bea73b7e44cc1aa6a38776d9f2053
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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