Acetylacetone → HCID 178426467, compound

HRID 722022Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([NH2:21])=[NH:20])[CH2:15][CH2:14]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22]([CH2:25][C:26](=O)[CH3:27])(=O)[CH3:23]>>[CH2:2]([O:9][C:10]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]2[N:21]=[C:26]([CH3:27])[CH:25]=[C:22]([CH3:23])[N:20]=2)[CH2:15][CH2:14]1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 31261Acetylacetone

HCID 178479354HCID 178479354, compound

Product 1

HCID 178426467HCID 178426467, compound

Procedure

Using trans-4-(benzyloxycarbonylamino)-1-cyclohexanecarboxamidine hydrochloride (a compound of Reference Example 8-35 (5)) (348 mg) as a starting material, by reacting the same with acetylacetone according to the method of Libman et al. (J. Chem. Soc., p. 2305, 1952), trans-1-benzyloxycarbonylamino-4-(4,6-dimethylpyrimidin-2-yl)cyclohexane (220 mg) was obtained. By treating this compound (205 mg) with trimethylsilyl iodide in the same manner as in Reference Example 8-35 (7), trans-4-(4,6-dimethylpyrimidin-2-yl)cyclohexylamine (Reference Example 8-36 in Table 9) (129 mg) was obtained.

Sources & evidence

ORD record: ord-db2ccf28acbc4267bc582bbb855ad56e
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138397B2

Reaction notes

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