Benzenamine, 3-ethynyl- → Ethyl 4-[(3-ethynylphenyl)amino]-5,8-dihydropyrido[4',3':4,5]furo[2,3-d]pyrimidine-7(6H)-carboxylate

HRID 38536

Reaction equation

HRID 38536 reaction equation
[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][C:6]=2[O:5][C:4]=1/[N:17]=[CH:18]/[N:19](C)C)#[N:2].[C:22]([C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)N)#[CH:23]>>[C:22]([C:24]1[CH:30]=[C:29]([NH:2][C:1]2[C:3]3[C:11]4[CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][C:6]=4[O:5][C:4]=3[N:17]=[CH:18][N:19]=2)[CH:28]=[CH:26][CH:25]=1)#[CH:23]

Participants

3

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 58116902ethyl 3-cyano-2-[(E)-dimethylaminomethylideneamino]-5,7-dihydro-4H-furo[2,3-c]pyridine-6-carboxylate

Product 1

HCID 58116811Ethyl 4-[(3-ethynylphenyl)amino]-5,8-dihydropyrido[4',3':4,5]furo[2,3-d]pyrimidine-7(6H)-carboxylate

Procedure

In analogy to Example 38A, the title compound was prepared from ethyl 3-cyano-2-{[(1E)(dimethylamino)methylidene]amino}-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylate from Example 37A (1.20 g, 4.14 mmol) and 3-ethynylaniline (968 mg, 8.27 mmol) to yield 443 mg (28%).

Workup

  1. customto yield 443 mg (28%)

Sources & evidence

ORD record
ord-084e91f3981f46cba9a252406bdee933
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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