Methanol → HCID 57818430, compound

HRID 705593Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([F:16])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][S:18][CH3:19].ClN1C(=O)CCC1=O.C[O-].[Na+].CO>C(Cl)Cl>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([N:15]=[S:18]([CH3:19])[CH3:17])[C:12]([F:16])=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 10 mL oven-dried Schlenk flask was charged with 2-(benzyloxy)-5-fluoropyrimidin-4-amine (101 mg, 0.462 mmol), CH2Cl2 (2 mL), and dimethylsulfide (75.0 μL, 1.02 mmol) and was cooled to 0° C. in an ice bath. N-Chlorosuccinimide (122 mg, 0.914 mmol) was added and the resulting mixture was allowed to stir at 0° C. for 45 minutes, and then at room temperature for 30 minutes. A solution of NaOMe in MeOH (25%, 360 μL, 1.35 mmol) was added. After 20 minutes, the reaction was quenched with water (3 mL) and allowed to stir for 1 hour. The crude reaction mixture was then diluted with CH2Cl2 and washed with water (50 mL×2), dried over anhydrous Na2SO4, filtered, and concentrated by rotary evaporation and then on high vacuum to give the title compound (120 mg, 93%) as an off white solid: mp 125-129° C.; 1H NMR (300 MHz, DMSO-d6): δ 7.70 (d, J=3.9 Hz, 1H), 7.25-7.44 (m, 5H), 5.21 (s, 2H), 2.75 (s, 6H); MS (ESI) m/z 281.1 (M+H)+. *Yamamoto, Y.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 4128-4129.

Workup

customA 10 mL oven-dried Schlenk flask
waitat room temperature for 30 minutes
waitAfter 20 minutes
customthe reaction was quenched with water (3 mL)
stirringto stir for 1 hour
customThe crude reaction mixture
washwashed with water (50 mL×2)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record: ord-c95425c1de1544d0911e84a6dbd82950
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174970B2

Reaction notes

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