Lithium Hydroxide → 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid

HRID 2093868Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([C:15]3[C:23]4[O:22][CH2:21][O:20][C:19]=4[CH:18]=[CH:17][C:16]=3[O:24][CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:9]=2[NH:8][CH:7]=1)=[O:5])C.[Li+].[OH-]>O1CCOCC1.O>[CH:26]1([CH2:25][O:24][C:16]2[CH:17]=[CH:18][C:19]3[O:20][CH2:21][O:22][C:23]=3[C:15]=2[C:14]2[C:9]3[NH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (9.53 g; 25.0 mmol) from example A48 is suspended in dioxane (170 mL) and water (100 mL). After addition of LiOH (2.99 g; 125.0 mmol) the reaction mixture is stirred at 100° C. over night. The resulting solution is evaporated to dryness. The residue is dissolved in hot (60-90° C.) water (250 mL) and pH is adjusted to 2-3 by addition of 2M citric acid while still hot. After cooling to ambient temperature the precipitated product is collected by suction filtration, washed with water, ethanol and dried in high vacuo at 50° C. to yield 8.22 g of the title compound as pale yellow solid.

Workup

customThe resulting solution is evaporated to dryness
dissolutionThe residue is dissolved in hot (60-90° C.) water (250 mL) and pH
additionis adjusted to 2-3 by addition of 2M citric acid while still hot
temperatureAfter cooling to ambient temperature the precipitated product
filtrationis collected by suction filtration
washwashed with water, ethanol
customdried in high vacuo at 50° C.

Sources & evidence

ORD record: ord-2d2bbfde5aea4cc09927c64ad55ff3b0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445501B2

Reaction notes

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