Citric Acid → HCID 16222003, compound

HRID 1896200Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[N:11]=[C:12](Cl)[C:13]2[N:18]([CH2:19][CH2:20][O:21][CH2:22][CH3:23])[N:17]=[C:16]([CH2:24][CH3:25])[C:14]=2[N:15]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:9][C:10]1[N:11]=[C:12]([NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=2)[C:13]2[N:18]([CH2:19][CH2:20][O:21][CH2:22][CH3:23])[N:17]=[C:16]([CH2:24][CH3:25])[C:14]=2[N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-amino-4-picoline (4.32 g, 40 mmol) and 5,7-dichloro-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidine from step 4 (5.78 g, 20 mmol) was treated with THF (25 mL) and cooled to 0° C. The mixture was stirred and treated with 1 M LiN(TMS)2 in THF (40 mL, 40 mmol) at a rate such that the temperature was kept below 5° C. The mixture was stirred for 30 min and was then treated with 10% citric acid solution until pH 6-7 was achieved. The mixture was partially concentrated under reduced pressure. The mixture was then stirred at 5° C. for 1 h. The resulting solid was collected by suction filtration and washed with water (40 mL). The solid was dried in a vacuum oven at a temperature less than 60° C. to afford 7.0 g of the title compound.

Workup

customwas kept below 5° C
stirringThe mixture was stirred for 30 min
concentrationThe mixture was partially concentrated under reduced pressure
stirringThe mixture was then stirred at 5° C. for 1 h
filtrationThe resulting solid was collected by suction filtration
washwashed with water (40 mL)
customThe solid was dried in a vacuum oven at a temperature less than 60° C.

Sources & evidence

ORD record: ord-0f894ce920364b4887f0aee463b55d83
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518956B2

Reaction notes

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