Piperazine, 1-(1-adamantyl)- → 1-(1-Adamantyl)-4-(2,6-diamino-4-pyrimidinyl)-piperazine

HRID 1768946

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([NH2:9])[N:3]=1.[C:10]12([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2>C(O)C>[C:10]12([N:20]3[CH2:25][CH2:24][N:23]([C:6]4[CH:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH2:1])[N:7]=4)[CH2:22][CH2:21]3)[CH2:17][CH:16]3[CH2:15][CH:14]([CH2:13][CH:12]([CH2:18]3)[CH2:11]1)[CH2:19]2

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 2,6-diamino-4-chloropyrimidine (0.43 g, 3.0 mmol) and 1-(1-adamantyl)-piperazine (0.66 g, 3.0 mmol) in ethanol (30 ml) was heated in a sealed tube at 170° C. for 3 hours. After cooling the solvent was removed, the solid residue was dissolved in water (45 ml) and acidified to pH=3 with conc. HCl. The obtained mixture was heated to 50° C. the insolubles were filtered off and the clear solution was rendered alkaline with 10N NaOH under stirring and cooling. The precipitated crystals were collected, washed with water until neutral and dried. In this manner 0.79 g of the title compound was obtained in the form of its monohydrate, yield: 76.6%, mp. 265°-268° C.

Workup

temperatureAfter cooling the solvent
customwas removed
dissolutionthe solid residue was dissolved in water (45 ml)
temperatureThe obtained mixture was heated to 50° C. the insolubles
filtrationwere filtered off
temperaturecooling
customThe precipitated crystals were collected
washwashed with water until neutral and
customdried

Sources & evidence

ORD record: ord-ffaac1866e2e41fd8560fdae32cb8b29
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380724

Linked notes

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