1,1'-Carbonyldiimidazole → (2,4-Dimethoxy-benzyl)-(2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester

HRID 1749099Notes

Reaction equation

HRID 1749099 reaction equation
[C:1](O)(=[O:3])C.[C:5]([O:9][C:10](=[O:32])[N:11]([C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([CH2:30][NH2:31])[N:24]=1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22])([CH3:8])([CH3:7])[CH3:6].C(N(CC)C(C)C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O>C1COCC1>[C:5]([O:9][C:10](=[O:32])[N:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22])[C:23]1[CH:28]=[CH:27][C:26]2[NH:29][C:1](=[O:3])[NH:31][CH2:30][C:25]=2[N:24]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 70980366(5-Amino-6-aminomethyl-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester acetate salt

Product 1

HCID 70981319(2,4-Dimethoxy-benzyl)-(2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl)-carbamic acid tert-butyl esterYield 43.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-amino-6-aminomethyl-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester acetate salt (1.3 g, 2.56 mmol) and N,N-diisopropylethylamine (890 μL, 5.12 mmol, 2 equiv) in THF (20 mL) was added a solution of 1,1′-carbonyldiimidazole (622 mg, 3.84 mmol, 1.5 equiv) and the reaction mixture was stirred overnight. The solvent was evaporated and the crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 50-100%) to afford (2,4-dimethoxy-benzyl)-(2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester (464 mg). MS: [M+H]+=415

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 50-100%)

Sources & evidence

ORD record
ord-2a95d3d91d58447c948a9d267e8e6ca9
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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