2-Chloro-4,6-dimethylpyrimidine → HCID 11327269, compound

HRID 898330Notes

Reaction equation

HRID 898330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([Cl:24])[N:18]=1>>[ClH:24].[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:19]3[N:20]=[C:21]([CH3:23])[CH:22]=[C:17]([CH3:16])[N:18]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11327269HCID 11327269, compound

Procedure

6-Bromo-N-(4,6-dimethylpyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine (50 mg, 0.19 mmol) and 4,6-dimethyl-2-chloropyrimidine (134 mg, 0.94 mmol) in a similar manner as described in Example 22 to give 12 mg (16%) of a yellow solid. 1H-NMR (DMSO-d6): δ10.98 (s, 1H), 8.40 (brs, 2H), 7.59 (s, 1H), 7.26 (d, 1H), 7.16 (d, 1H), 6.77 (s, 1H), 5.52-5.48 (m, 1H), 2.68-2.61 (m, 2H), 2.41 (2 s, 6H), 2.15-2.06 (m, 1H), 2.04-1.96 (m, 1H), 1.91-1.76 (m, 2H); MS m/z (M+1) 371, 373; (M−1) 369, 371.

Sources & evidence

ORD record
ord-cfaac78bcfa14b7a8acc5f28d18bad65
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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