Tetrahydrofuran → HCID 57632789, compound

HRID 2109805Notes

Reaction equation

HRID 2109805 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4](=O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)=[CH:9][CH:8]=1)[CH3:2].[Li].C1COCC1>CO>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]2[N:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)=[CH:18][N:19]=2)=[CH:11][CH:12]=1)[CH3:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 57632944HCID 57632944, compound

Product 1

HCID 57632789HCID 57632789, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N-Diethyl-3-{4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionamide (0.1 mmol) is heated at reflux with lithium alluminium hydride in THF (1.0 M, 1.0 mmol) for 4 h. MeOH is added at rt to quench the reaction. Purification by preparative LCMS affords the title compound. 1H NMR (400 MHz, CDCl3) δ 12.4 (s, 1H), 8.62 (s, 2H), 8.59 (s, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H), 7.02 (d, J=8.6 Hz, 2H), 3.86 (s, 3H), 3.1 (m, 4H), 3.96 (s, 1H), 3.0 (m, 2H), 2.71 (t, J=7.2, 2H), 2.06 (m, 2H), 1.27 (t, J=7.3 Hz, 6H). MS (m/z) (M+1)+ 391.2.

Workup

  1. customto quench
  2. customthe reaction
  3. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-0ee8205d54f542f886f20689ac9adb4d
Source dataset
uspto-grants-2009_04
Patent number
US07514447B2

Reaction notes

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