1-Phenylpiperazine → HCID 10293109, compound

HRID 1838175Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([NH:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=1.C(N(C(C)C)C(C)C)C.[C:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCOCC1>[CH:15]1([NH:14][C:4]2[N:5]=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[C:7]([C:8]#[N:9])=[C:2]([N:36]3[CH2:37][CH2:38][N:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:34][CH2:35]3)[N:3]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 70 mg (0.27 mmol) of 4-chloro-2-cyclopropylamino-6-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile and 0.047 ml (0.27 mmol) of N-ethyl-diisopropylamine in 5 ml of dioxane was treated with 49 mg (0.3 mg) of 1-phenyl-piperazine. The solution was heated to 100° C. during 18 hours, thereafter, for the working-up, evaporated under reduced pressure. For purification, the residue obtained was chromatographed by preparative HPLC on RP18-silica gel using a gradient of a mixture of acetonitrile and water (plus 0.1% of formic acid) as the eluent to give 60 mg (0.16 mmol, 58% of theory) of the 2-cyclopropylamino-4-(2-hydroxy-ethylamino)-6-(4-phenyl-piperazin-1-yl)-pyrimidine-5-carbonitrile as a white powder after lyophilization; MS: [M+H]+=380.

Workup

customevaporated under reduced pressure
customFor purification
customthe residue obtained
customwas chromatographed by preparative HPLC on RP18-silica gel using
additiona gradient of a mixture of acetonitrile and water (plus 0.1% of formic acid) as the eluent

Sources & evidence

ORD record: ord-8c6b75949220456abb56cd655ba55822
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673795B2

Reaction notes

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