HCID 75204436, compound → HCID 75204437, compound

HRID 1755257Notes

Reaction equation

HRID 1755257 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[N:6][C:7]([C:10]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]4[N:20]([CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:22][N:23]=3)[CH2:14]2)=[O:11])=[N:8][CH:9]=1)[CH3:3]>CO.[Pd]>[CH:2]([C:4]1[CH:9]=[N:8][C:7]([C:10]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]4[N:20]([CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:22][N:23]=3)[CH2:14]2)=[O:11])=[N:6][CH:5]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 75204436HCID 75204436, compound

Product 1

HCID 75204437HCID 75204437, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-5-(prop-1-en-2-yl)-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.090 g, 0.26 mmol, 1 eq) in 1 mL of MeOH was added 10% Pd/C (0.027 g, 0.03 mmol, 0.1 eq). The reaction mixture was equipped with a H2 balloon and stirred for 1 hr at room temperature. The contents were filtered and the purified by HPLC to afford (S)-5-isopropyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.048 g, 0.14 mmol, 53%). 1H NMR (400 MHz, CD3OD) δ 8.81 (s, 2 H), 7.76 (s, 1 H), 7.71 (d, J=5.8 Hz, 1 H), 7.55 (s, 1 H), 6.92 (s, 1 H), 6.84 (d, J=5.9 Hz, 1 H), 5.00-3.60 (br, 5 H), 3.18-3.00 (m, 1 H), 2.65-2.30 (br, 2 H), 1.36 (d, J=7.0 Hz, 6 H); MS: (ES) m/z calculated for C19H22N6O [M+H]+ 351.2, found 351.

Workup

  1. customThe reaction mixture was equipped with a H2 balloon
  2. filtrationThe contents were filtered
  3. customthe purified by HPLC

Sources & evidence

ORD record
ord-43389cf018a7442484f93da8cc396760
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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