Carbon Dioxide → 4-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)benzoic acid

HRID 227611Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.C([Li])CCC.[C:24](=[O:26])=[O:25].Cl>C1COCC1.O>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:24]([OH:26])=[O:25])=[CH:3][CH:4]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A −78° C. solution of Example 66A (1.5 g, 4.68 mmol) in THF (50 mL) was treated dropwise with 2.5M n-butyllithium in hexanes (4.7 mL, 11.71 mmol), stirred for 30 minutes at −78° C., then treated with excess dry ice. The reaction was stirred at −78° C. for 30 minutes, warmed to room temperature, diluted with water, adjusted to pH 3 with 2N HCl, and filtered. The filter cake was dried to provide 686 mg (51%) of the desired product. MS (CI) m/e 285 (M+); 1H NMR (300 MHz, DMSO-d6) δ 13.13 (br s, 1H); 8.29 (s, 1H); 8.09 (d, J=8.4 Hz, 2H); 7.53 (d, J=8.4 Hz, 2H); 2.28 (s, 3H).

Workup

stirringThe reaction was stirred at −78° C. for 30 minutes
temperaturewarmed to room temperature
filtrationfiltered
customThe filter cake was dried

Sources & evidence

ORD record: ord-dc1c730fb6b94991b38e057c7a617aff
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560552B2

Reaction notes

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