Triethylamine → HCID 68708811, compound

HRID 645525Notes

Reaction equation

HRID 645525 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([NH:23]C(OCC=C)=O)=[C:21]([NH:30][CH2:31][CH:32]3[CH2:40][CH2:39][C:35]4([CH2:38][CH2:37][CH2:36]4)[CH2:34][CH2:33]3)[N:20]=[C:19]([C:41]#[N:42])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([NH2:23])=[C:21]([NH:30][CH2:31][CH:32]3[CH2:40][CH2:39][C:35]4([CH2:38][CH2:37][CH2:36]4)[CH2:34][CH2:33]3)[N:20]=[C:19]([C:41]#[N:42])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 68703130HCID 68703130, compound

Product 1

HCID 68708811HCID 68708811, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude 4-(2-{5-allyloxycarbonylamino-2-cyano-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester (230 mg) in THF (10 mL) are added trietylamine (1.25 mmol) and Pd(PPh3)4 (catalytic amount) at room temperature under N2 atmosphere. After stirring at the same temperature for 1 h, the reaction mixture is diluted with AcOEt. The organic layer is washed with H2O and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give 4-(2-{5-Amino-2-cyano-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester; 1H-NMR (CDCl3), δ: 0.97-1.07 (2H, m), 1.13-1.28 (4H, m), 1.42-1.88 (25H, m), 2.69 (2H, t), 3.22 (2H, s), 3.31 (2H, t), 4.04-4.16 (2H, m), 4.40 (2H, t), 4.51 (1H, t).

Workup

  1. washThe organic layer is washed with H2O
  2. customevaporated in vacuo
  3. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-270bec02e9234692ad98c330e4593188
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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