1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-amino-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1666258Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5](/[CH:11]=[CH:12]/[C:13](OCC)=[O:14])=[C:4]([CH3:18])[N:3]=1.C1CCN2C(=NCCC2)CC1>O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:18])[C:5]2[CH:11]=[CH:12][C:13](=[O:14])[N:8]([CH2:9][CH3:10])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 165 °C

Procedure

(E)-Ethyl 3-(2-amino-4-(ethylamino)-6-methylpyrimidin-5-yl)acrylate (4.50 g, 18.0 mmol) was added to DBU (10.95 g, 4.0 equiv.) and the mixture was heated to 165° C. and stirred for 24 h. After that, the mixture was cooled to 70° C. followed by the addition of H2O (20 mL) to precipitate crystal and stirred for 1 h at room temperature. The crystal was collected and washed with H2O and acetone and dried under vacuum to afford 2.70 g (73.5% yield of 2-amino-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one as a light yellowish brown solid. LC/MS: Calculated for C10H12N4O (204.2). Found: 205.31 (M+1); HPLC analytical purity: 98.5%. 1H NMR (400 MHz, DMSO-d6): δ 7.9 (d, 1H), 7.20 (bs, 2H), 6.20 (m, 1H), 4.20 (q, 2H), 2.50 (s, 3H), 1.20 (t, 3H); MS (EI) for C10H12N4O: 205.11 (MH+).

Workup

temperatureAfter that, the mixture was cooled to 70° C.
customto precipitate crystal
stirringstirred for 1 h at room temperature
customThe crystal was collected
washwashed with H2O and acetone
customdried under vacuum

Sources & evidence

ORD record: ord-6e886d7c80cf4be492b79a66c8c55823
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044062B2

Reaction notes

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