Ethyl orthoformate → 3-(4-Isopropylcyclohexyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775701Notes

Reaction equation

HRID 1775701 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:24]1[C:28](C2C=CC=CC=2)=CS[C:25]=1C(OC)=O.C(OCC)(OCC)OCC.C(C1CCC(N)CC1)(C)C>C(O)(=O)C>[CH:24]([CH:4]1[CH2:5][CH2:6][CH:1]([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:10]=3[N:9]=[CH:8]2)[CH2:2][CH2:3]1)([CH3:28])[CH3:25]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 4210534-IsopropylcyclohexylamineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 867298183-(4-Isopropylcyclohexyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-oneYield 58.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-phenylthiophene-2-carboxylate (100 mg, 0.43 mmol), triethyl orthoformate (1 ml), 4-isopropylcyclohexylamine (0.148 ml, 0.90 mmol), and acetic acid (0.1 ml) were used to give 88.5 mg (0.25 mmol, 58.4% yield) of the title compound.

Sources & evidence

ORD record
ord-099fe8b9832c49b0837be2da14faa757
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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