Diisopropylethylamine → 2-chloro-N-(5-isopropyl-1H-pyrazol-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

HRID 1485293Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.[CH:21]([C:24]1[NH:28][N:27]=[C:26]([NH2:29])[CH:25]=1)([CH3:23])[CH3:22]>C(O)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:29][C:26]2[CH:25]=[C:24]([CH:21]([CH3:23])[CH3:22])[NH:28][N:27]=2)[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, Compound (i) (8 g, 42 mmol) in isopropanol (100 mL) was added N,N-diisopropylethyl amine (8.67 g, 67 mmol) followed by 5-isopropyl-1H-pyrazol-3-amine, Compound (ii) (5.89 g, 47 mmol). The reaction mixture was heated to reflux at 100° C. for 16 h. The reaction mixture was cooled to RT. The precipitated product was filtered and washed with hexane to afford 2-chloro-N-(5-isopropyl-1H-pyrazol-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine, Compound (iii) (5 g, 42%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1.22 (d, 6H), 1.96-2.07 (m, 2H), 2.70-2.81 (m, 4H), 2.88-3.01 (m, 1H), 6.38 (s, 1H), 9.60 (s, 1H), 12.11 (brs, 1H).

Workup

temperatureThe reaction mixture was heated
temperatureThe reaction mixture was cooled to RT
filtrationThe precipitated product was filtered
washwashed with hexane

Sources & evidence

ORD record: ord-4320c37ac0ae49c5abc99b18b2d7351c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422267B2

Reaction notes

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