Water → HCID 86692141, compound

HRID 527918Notes

Reaction equation

HRID 527918 reaction equation
C[C@@H:2]1[CH:6]([NH:7][CH3:8])[CH2:5][CH2:4][N:3]1[C:9]1[C:10]2[CH:17]=[CH:16][NH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[N:12]1[C:11]2[NH:15][CH:16]=[CH:17][C:10]=2[C:9]([N:3]2[CH2:4][CH2:5][C@@H:6]([N:7]([CH3:8])[C:21]3[CH:22]=[CH:23][N:24]=[C:19]([Cl:18])[N:20]=3)[CH2:2]2)=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 86692142HCID 86692142, compound

Product 1

HCID 86692141HCID 86692141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl (R)—N-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (0.20 g, 0.92 mmol), 2,4-dichloropyrimidine (0.18 g, 1.21 mmol) and DIPEA (0.25 g, 1.94 mmol) in DMF (6 mL) was stirred at 110° C. for 16 hours. The mixture was poured into water (5 mL) and extracted with ethyl acetate (2×8 mL). The combined extracts was washed with brine (2×30 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (v. DCM/MeOH=12/1) to give the title compound. MS (m/z): 330 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×8 mL)
  2. washThe combined extracts was washed with brine (2×30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (v. DCM/MeOH=12/1)

Sources & evidence

ORD record
ord-3420312611e54fe2a276668b73daf0a1
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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