Hydrazine hydrate (1:1) → 6-(3-Amino-1H-indazol-6-yl)-N4-(1,1-dimethyl-2-phenylethyl)-2,4-pyrimidinediamine

HRID 2367262Notes

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][C:18]([CH3:27])([CH3:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.O.[NH2:29][NH2:30]>C(O)C>[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][C:18]([CH3:27])([CH3:26])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:30][N:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-{2-amino-6-[(1,1-dimethyl-2-phenylethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (210 mg, 0.58 mmol) and hydrazine hydrate (99%, 2 mL) in ethanol (3 mL) was stirred and heated at 120° C. for 1 h in a Biotage Initiator microwave synthesizer. The mixture was cooled to room temperature and concentrated in vacuo. Water (100 mL) was added, and the resulting mixture was filtered. The solids were dried under vacuum to afford the title compound (90 mg) as a yellow solid. LC-MS (ES) m/z=374 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.34 (s, 6H), 3.26 (s, 2H), 5.37 (s, 2H), 6.05 (s, 2H), 6.34 (s, 1H), 6.40 (s, 1H), 7.10-7.25 (m, 5H), 7.39 (d, 1H), 7.70 (d, 1H), 7.84 (s, 1H).

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
additionWater (100 mL) was added
filtrationthe resulting mixture was filtered
customThe solids were dried under vacuum

Sources & evidence

ORD record: ord-6ddc2b04178b489994e80891d3218bf1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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