Triethylamine → HCID 178433415, compound

HRID 841016Notes

Reaction equation

HRID 841016 reaction equation
Br[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][C:14]1[N:15]=[C:16]([OH:25])[C:17]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][C:18]=2[N:24]=1.C(N(CC)CC)C>[Pd].CN(C)C=O>[OH:9][C:4]1[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([N:21]2[CH2:22][CH2:23][C:17]3[C:16]([OH:25])=[N:15][C:14]([CH3:13])=[N:24][C:18]=3[CH2:19][CH2:20]2)[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1356171936-bromo-2-methyl-5-nitro-3H-pyrimidin-4-oneHCID 178433416HCID 178433416, compound

Product 1

HCID 178433415HCID 178433415, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 1c 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one (example. 1a) was treated with the 2-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (prepared from the corresponding N-benzyl derivative [Bull. Chem. Soc. Jap. (1971), 44(1), 153-8] by catalytic hydrogenation with palladium on charcoal) in N,N-dimethylformamide in the presence of triethylamine at room temperature to yield the title compound as yellow solid; m.p.>200° C.; MS: [M+H]+=333.

Sources & evidence

ORD record
ord-fa7384df28ef4e22a81fd7ede600e064
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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