N-[3-carboxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine → N-[3-carboxy-phenyl]-4-[2-(4-amino-butyl-amino)-4-pyridyl]-2-pyrimidineamine

HRID 859105Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](Cl)[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]>NCCCCN>[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:16][CH2:15][CH2:17][CH2:18][CH2:19][NH2:20])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-[3-carboxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (99 mg, 0.30 mmol) in 1,4-diaminobutane (1.5 mL) is heated to 110° C. overnight, cooled to room temperature and concentrated. The residue is dissolved in water and neutralized with 10% hydrochloric acid. The reaction mixture is purified by preparative HPLC to give N-[3-carboxy-phenyl]-4-[2-(4-amino-butyl-amino)-4-pyridyl]-2-pyrimidineamine (84 mg); ESI-MS (m/z): 379 (M++H).

Workup

temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue is dissolved in water and neutralized with 10% hydrochloric acid
customThe reaction mixture is purified by preparative HPLC

Sources & evidence

ORD record: ord-119f9f38da2a41d3a171c7d28e831c10
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151096B2

Reaction notes

Loading…