Hydrazine hydrate (1:1) → HCID 46214652, compound

HRID 2367183Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][CH2:18][CH3:19])[N:3]=1.O.[NH2:21][NH2:22]>CC#N.CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH2:18][CH3:19])[CH:5]=3)=[CH:15][CH:14]=2)[NH:22][N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 25 mL flask under argon was added 4-[2-amino-6-(ethylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (0.164 g, 0.442 mmol) followed by EtOH (3.5 mL). Hydrazine monohydrate (0.87 mL, 17.7 mmol) was added and the reaction mixture was stirred for 6 hours at 80° C. The reaction was cooled to room temperature and concentrated to near dryness. Water (3 mL) was added (orange oil was formed) followed by CH3CN (8 drops), and the mixture was sonicated. A light yellow precipitate was formed. The suspension was cooled on an ice bath and the solid was filtered, washed with water and dried under vacuum at 40° C. to afford the title compound (82 mg, 68%) as a light yellow solid. LC-MS (ES) m/z=270 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.13 (t, J=7.2 Hz, 3H), 3.20-3.40 (m, 2H), 5.36 (s, 2H), 5.97 (s, 2H), 6.25 (s, 1H), 6.82 (bs, 1H), 7.41 (d, J=8.3 Hz, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.84 (s, 1H), 11.50 (s, 1H).

Workup

temperatureThe reaction was cooled to room temperature
concentrationconcentrated
additionWater (3 mL) was added
custom(orange oil was formed)
customthe mixture was sonicated
customA light yellow precipitate was formed
temperatureThe suspension was cooled on an ice bath
filtrationthe solid was filtered
washwashed with water
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-4753264bad7f41b48cff1c73bcf48f36
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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