2-Amino-2-methyl-1,3-propanediol → HCID 72709531, compound

HRID 1482882Notes

Reaction equation

[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]([NH:30][C:31]3[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=3)[CH:26]=[C:27]([CH3:29])[CH:28]=2)=[CH:19][N:18]=1>CS(C)=O>[CH3:7][C:2]([NH:1][C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:24]=[C:25]([NH:30][C:31]3[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=3)[CH:26]=[C:27]([CH3:29])[CH:28]=2)=[CH:19][N:18]=1)([CH2:5][OH:6])[CH2:3][OH:4]

Participants

Conditions

Temperature: 130 °C

Procedure

2-Amino-2-methyl-1,3-propanediol (28.7 mg, 0.273 mmol), potassium phosphate, tribasic (58 mg, 0.273 mmol), and N-[3-(2-chloropyrimidin-5-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (50 mg, 0.137 mmol) were dissolved in DMSO (300 μL). The mixture was heated to 130° C. for 48 hours, and then allowed to cool to room temperature. The mixture was diluted with DMSO (0.7 mL), filtered, and purified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water+0.1% formic acid) to afford 2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyrimidin-2-yl]amino}propane-1,3-diol. MS ESI calcd for C20H22F3N6O2 [M+H]+ 332. found 332. 1H NMR (600 MHz, DMSO-d6) δ 10.17 (s, 1H), 8.80 (d, J=5.2 Hz, 1H), 8.52 (d, J=23.4 Hz, 2H), 7.82 (s, 1H), 7.43 (s, 1H), 7.23 (d, J=5.1 Hz, 1H), 7.08 (s, 1H), 6.36 (s, 1H), 3.60-3.50 (m, 4H), 2.30 (s, 3H), 1.25 (d, J=12.1 Hz, 3H).

Workup

temperatureto cool to room temperature
filtrationfiltered
custompurified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water+0.1% formic acid)

Sources & evidence

ORD record: ord-f5ac1acdc0154eb881038df7992a90fc
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416111B2

Reaction notes

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