Potassium Carbonate → HCID 86623469, compound

HRID 639488Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[C:8]2[N:9]=[C:10]([NH2:14])[N:11]=[C:12]([Cl:13])[C:7]=2[CH:6]=[CH:5]1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][C:12]1[C:7]2[CH:6]=[CH:5][N:4]([CH2:3][CH2:2][N:26]3[CH2:25][CH2:24][N:23]([C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[F:15])[CH2:28][CH2:27]3)[C:8]=2[N:9]=[C:10]([NH2:14])[N:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the title A compound in Example 29, 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (225 mg, 0.817 mmol) and 1-(2,4-difluorophenyl)piperazine (193 mg, 0.976 mmol) in 1 mL of dry acetone is added potassium carbonate (322 mg, 2.44 mmol). The mixture is heated at 50° C. for 24 h, cooled to RT, concentrated in vacuo, and the residue taken up in water. The aqueous mixture is repeatedly extracted with EtOAc, and the combined organic extracts are dried (Na2SO4), filtered and evaporated to dryness. The residue is purified by column chromatography on silica gel, eluting with 2% MeOH in DCM to afford 4-chloro-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine as a yellow solid: 1H NMR (CDCl3) δ 2.68 (m, 4H), 2.77 (t, 2H, J=8.0 Hz), 3.01 (m, 4H), 4.19 (t, 2H, J=8.0 Hz), 4.88 (br s, 2H), 6.36 (d, 1H, J=4.0 Hz), 6.77-6.87 (m, 3H), 6.96 (d, 1H, J=4.0 Hz).

Workup

temperaturecooled to RT
concentrationconcentrated in vacuo
extractionThe aqueous mixture is repeatedly extracted with EtOAc
dry with materialthe combined organic extracts are dried (Na2SO4)
filtrationfiltered
customevaporated to dryness
customThe residue is purified by column chromatography on silica gel
washeluting with 2% MeOH in DCM

Sources & evidence

ORD record: ord-9d07cc6e28014664b1ae5fb4997bbcbe
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691869B2

Reaction notes

Loading…