Carbon Tetrachloride → 2-Iodo-4-(6-methyl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenol hydrochloride

HRID 1937407Notes

Reaction equation

[CH3:1][C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:33].[OH:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][C:39]=1[I:45]>ClCCCl>[ClH:33].[I:45][C:39]1[CH:40]=[C:41]([NH:42][C:9]2[C:4]3[CH:3]=[C:2]([CH3:1])[N:12]=[CH:11][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:43]=[CH:44][C:38]=1[OH:37]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Methyl-pyrido[3,4-d]pyrimid-4-one (161 mg, 1.00 mmol) was added to polymer-supported triphenylphosphine (1.66 g of about 3 mmol P/g polymer; 5.0 mmol) along with CCl4 (1.54 g, 10.0 mmol) in 1,2-dichloroethane (6 mL). The reaction mixture was heated to 60° C. for 2 hours and then the resin was filtered and washed with 1,2-dichloroethane. The filtrate was collected in a flask containing 4-hydroxy-3-iodo-aniline (0.235 g, 1.00 mmol) and concentrated to 5 mL by evaporation. After 12 hours reflux under nitrogen followed by cooling to 20° C., the title product was collected by filtration (347 mg; 83%; M.P. 261-265° C.; LC-MS: 379 (MH+); anal. RP-HPLC: 3.20 min.).

Workup

filtrationthe resin was filtered
washwashed with 1,2-dichloroethane
customThe filtrate was collected in a flask
concentrationconcentrated to 5 mL by evaporation
temperatureAfter 12 hours reflux under nitrogen
temperatureby cooling to 20° C.
filtrationthe title product was collected by filtration (347 mg; 83%; M.P. 261-265° C.; LC-MS: 379 (MH+); anal. RP-HPLC: 3.20 min.)

Sources & evidence

ORD record: ord-736db1f4682b48e3bc669b202e69d9ba
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395733B1

Reaction notes

Loading…