Morpholine → N-(1-Methyl-1H-pyrazol-4-yl)-1-((6-morpholinopyridin-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 577264Notes

Reaction equation

HRID 577264 reaction equation
F[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:13]3=[N:14][C:15]([NH:18][C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[N:16][CH:17]=[C:12]3[CH:11]=[N:10]2)[CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(Cl)Cl>[CH3:24][N:22]1[CH:23]=[C:19]([NH:18][C:15]2[N:14]=[C:13]3[N:9]([CH2:8][C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[N:7]=4)[N:10]=[CH:11][C:12]3=[CH:17][N:16]=2)[CH:20]=[N:21]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 667652621-((6-Fluoropyridin-2-yl)methyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 66765502N-(1-Methyl-1H-pyrazol-4-yl)-1-((6-morpholinopyridin-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

1-((6-fluoropyridin-2-yl)methyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (27 mg, 0.08 mmol) was dissolved in morpholine (0.6 ml) in a microwave tube under Nitrogen which was sealed and heated at 180° C. for 1 h. The mixture was diluted with DCM, washed with water and the water re-extracted with DCM. The combined organics were dried over Na2SO4, filtered and the solvent evaporated to give the title compound as a yellowish solid (20 mg, 64% yield). 1H NMR (d6-DMSO) δ 9.78 (br s, 1H), 8.91 (s, 1H), 8.05 (s, 1H), 7.91 (s, 1H), 7.52 (s, 1H), 7.46 (t, 1H), 6.68 (d, 1H), 6.28 (br s, 1H), 5.46 (s, 2H), 3.78 (s, 3H), 3.62 (t, 4H), 3.35 (t, 4H); LC-MS method B, (ES+) 392.0, RT=6.84 min.

Workup

  1. customwas sealed
  2. washwashed with water
  3. extractionthe water re-extracted with DCM
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-ae6b8dad8e0145ee95501577ac5f90ac
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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