Water → 3-(Tetrahydrofuran-3-yl oxy)-4-(thieno[3,2-d]pyrimidin-4-yl amino)-benzamide

HRID 472018Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][CH:12]1[CH2:16][CH2:15][O:14][CH2:13]1.Cl[C:18]1[C:19]2[S:26][CH:25]=[CH:24][C:20]=2[N:21]=[CH:22][N:23]=1.[OH-].[NH4+].O>CC(O)C>[O:14]1[CH2:15][CH2:16][CH:12]([O:11][C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=2[NH:1][C:18]2[C:19]3[S:26][CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[C:6]([NH2:8])=[O:7])[CH2:13]1

Participants

Conditions

Temperature: 120 °C

Procedure

The reaction was carried out in 4 batches using ACE pressure tubes. The 4-amino-3-(tetrahydrofuran-3-yloxy)-benzamide (0.52 g, 1.0 eq, 2.34 mmol) was added to a solution of 4-chlorothieno[3,2-d]pyrimidine (0.40 g, 1.0 eq, 2.34 mmol) in IPA (4 ml). The reaction mixtures were then stirred at 120° C. for 18 hours before being allowed to cool. 28% w/w Ammonium hydroxide solution (4 ml) followed by water (8 ml) were added and the reactions combined. The precipitate was isolated by filtration, washed with water (4×50 ml), dried on the sinter, washed with cyclohexane (8×50 ml), and then dried in vacuo to give the title compound as an off-white solid (2.71 g, 7.6 mmol, 81%). LCMS: [M+H]+=357; Rt=1.27 min, 100% purity.

Workup

customThe reaction mixtures
temperatureto cool
additionwere added
customThe precipitate was isolated by filtration
washwashed with water (4×50 ml)
customdried on the sinter
washwashed with cyclohexane (8×50 ml)
customdried in vacuo

Sources & evidence

ORD record: ord-76dcb12d79764932aed053bdefec2a1b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633201B2

Reaction notes

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