Methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate → 4-(4-Carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 450530Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[C:19]([CH3:20])=[C:18]([C:21]([O:23]C)=[O:22])[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[NH2:2]>[OH-].[NH4+]>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[C:19]([CH3:20])=[C:18]([C:21]([OH:23])=[O:22])[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.025 g, 0.06 mmol) in ammonium hydroxide (1.5 mL) was heated at 150° C. in a sealed-tube for 16 hours. The ammonium hydroxide was concentrated in vacuo and the residue redissolved in dimethyl sulfoxide. The sample was purified by reverse phase preparative HPLC to yield white solid (0.007 g, 29%).

Workup

concentrationThe ammonium hydroxide was concentrated in vacuo
dissolutionthe residue redissolved in dimethyl sulfoxide
customThe sample was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-12782c7a06fd494f8beeceb9be3933ed
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486953B2

Reaction notes

Loading…